SYNTHESIS OF (-)-(5R, 6S)-6-ACETOXY-5-HEXADECANOLIDE A PHEROMONE
Main Article Content
Keywords
Phermone, synthesis, Grignard reaction, Wittig-Horner reaction, Magnesium mediated electron transfer reduction, D-ribose
Abstract
Synthetic methodology developed for (–)-(5R, 6S)-erythro-6-acetoxy-5-hexadecanolide,which is a D-ribose based synthetic pheromone used to promote mosquito oviposition. The important steps involved are Grignard reaction, oxidative cleavage of 1,2-diol followed by Wittig-Horner reaction, lactonization with magnesium and acetylation.
References
1. Mori K, Otsuka T. Synthesis of both the enantiomers of erythro-6-acetoxy-5- hexadecanolide: The major component of a mosquito oviposition attractant pheromone. Tetrahedron Lett 1983;39:3267-9. https://doi.org/10.1016/S0040-4020(01)91574-1
2. Grubbs RH. Olefin metathesis. Tetrahedron 2004;60:7117-40. https://doi.org/10.1016/j. tet.2004.05.124
3. Furstner A. Recent Advancements in ring closing Olefin Metathesis. Top Catal
1997;4:285-99. https://doi.org/10.1023/A:1019117012154
4. Otieno WA, Onyango TO, Pile MM, Laurence BR, Dawson GW, Wadhams LJ, Pickett JA. A field trial of the synthetic oviposition pheromone with Culex quinquefasciatus say (Diptera: Culicidae) in Kenya. Bull. Entomol. Res. 1988;78:463-70. https://doi.org/10.1017/S000748 5300013213
5. Dawson GW, Laurence BR, Pickett JA, Pile MM, Wadhams LJ. A note on the mosquito oviposition pheromone. Pestic. Sci. 1989;27:277-80. https://doi.org/10.1002/ps.2780270307
6. Blackwell A, Mordue (Luntz) AJ, Hansson BS, Wadhams LJ, Pickett JAA, A behavioural and electrophysiological study of ovi position cues for Culex quinquefasciatus. Physiol Entomol 1993;18:343-8. https://doi.org/10.1111/j.1365-3032.1993.tb00607.x
7. Fuganti C, Grasselli P, Servi SJ. Synthesis of the two enantiomeric forms of erythro-6-acetoxy-5- hexadecanolide, the major component of a mosquito oviposition attractant pheromone. J Chem Soc. Chem. Commun. 1982; 8:1285–6. https://doi.org/10.1039/C39820001285
8. Park Y, Tae J, Facile synthesis of (-)-6-Acetoxy-5-hexadecanolide by organocatalytic α- oxygenation-allylation-RCM Strategy. Synthesis 2010;21:3627–30. https://doi.org/10.1055/s-0030-1258248
9. Singh S, Guiry PJ, A facile synthesis of both enantiomers of 6-acetoxy-5-hexadecanolide, a major component of mosquito oviposition attractant pheromones. Eur. J. Org. Chem. 2009;12: 1896-1901. https://doi.org/10.1002/ejoc.200801134
10. Quinn KJ, Curto JM, McGrath KP, Biddick NA. Facile synthesis of (−)-6-acetoxy-5- hexadecanolide by size-selective ring-closing/cross metathesis. Tetrahedron Lett 2009;50: 7121–7123. https://doi.org/10.1016/j.tetlet.2009.09.179
11. Prasad KR, Anbarasan P. Stereoselective synthesis of (−)-6-acetoxyhexadecanolide: a mosquito oviposition attractant pheromone. Tetrahedron: Asymmetry 2007;18:2479–83. https://doi.org/ 10.1016/j.tetasy.2007.10.006
12. Ikishima H, Sekiguchi Y, Ichikawa Y, Kotsuki H. Synthesis of (−)-(5R,6S)-6- acetoxyhexadecanolide based on L-proline-catalyzed asymmetric aldol reactions Tetrahedron, 2006;62:311–6. https://doi.org/10.1016/j.tet.2005.08.111
13. Das S, Mishra AK, Kumar A, Ghamdi AAKA, Yadav JS. Facile total synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide from carbohydrate, a mosquito oviposition attractant pheromone. Carbohydr. Res. 2012;358:7-11. https://doi.org/10.1016/j.carres.2012.05.009
14. Dhotare B, Goswami D, Chattopadhyay A. (R)-2,3-Cyclohexylideneglyceraldehyde, a novel template for stereoselective preparation of functionalized δ-lactones: synthesis of mosquito oviposition pheromone. Tetrahedron Lett 2005;46:6219-21. https://doi.org/10.1016/j.tetlet. 2005. 07.063
15. Sun B, Peng L, Chen X, Li Y, Yamasaki K. Synthesis of (−)-(5R,6S)-6-acetoxyhexadecan-5-olide by L-proline-catalyzed asymmetric aldol reactions. Tetrahedron: Asymmetry 2005;16:1305-7. https://doi.org/10.1016/j.tetasy.2005.02.017
16. Gao X, Hall DG. 3-Boronoacrolein as an Exceptional Heterodiene in the Highly Enantio-and Diastereoselective Cr(III)-Catalyzed Three-Component [4+2]/Allylboration. J Am Chem Soc 2003;125:9308–9. https://doi.org/10.1021/ja036368o
17. Gallos JK, Mihelakis DS, Dellios CC, Pozarentzi ME. Heterocycles. 2000;53:703–707, Couladouros EA, Mihou AP. A general synthetic route towards γ- and δ-lactones. Total asymmetric synthesis of (−)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide. Tetrahedron Lett 1999;40: 4861–2. https://doi.org/10.1016/S0040-4039(99)00895-3
18. Lohray BB, Venkateswarlu S. Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone. Tetrahedron: Asymmetry 1997;8: 633–8.https://doi.org/10.1016/S0957-4166(97)00011-6
19. Carlo B, Checconi M, Righi G, Rossi L. Enantio and stereoselective synthesis of (5R,6S )-6- acetoxy- hexadecanolide, a Mosquito Oviposition attractant pheromone. Tetrahedron 1995;51: 4111–6. https://doi.org/10.1016/0040-4020(95)00128-U
20. Gravier-Pelletier C, Le Merrer Y, Depezay JC. Enantiopure hydroxylactones from L- ascorbic and D-isoascorbic acids. Part II. Synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide and its diastereomers. Tetrahedron 1995;51:1663–74. https://doi.org/10.1016/0040-4020(94)01033-V
21. Coutrot P, Bomont CG. 5-formyl-δ—valerolactone: A useful synthon for the chiralsynthesis of the vespa orientalis pheromone and the mosquito oviposition attractant pheromone. Tetrahedron Lett 1994;35:8381–4. https://doi.org/10.1016/S0040-4039(00)74412-1
22. Ramaswamy S, Oehlschlager AC. Chemico-microbial syntheses of Japanese beetle and mosquito oviposition pheromones. Tetrahedron 1991;47:1145–56. https://doi.org/10.1016/S0040-4020(01) 86371-7
23. Wu W, Wu YJ. A concise synthesis of the natural mosquito Oviposition attractant pheromone from D-Glucose. Carbohydr. Chem. 1991;10:279–81. https://doi.org/10.1080/ 07328309108543907
24. Wang ZM, Qian XH, Zhou WS. Stereoselective synthesis of (-)-(5R,6S)-6-acetoxy-5- hexadecanolide, the mosquito oviposition attractant pheromone. Tetrahedron 1990;46:1191–6. https://doi.org/10.1016/S0040-4020(01)86684-9
25. Kotsuki H, Kadota I, Ochi M. A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor. J Org Chem 1990;55:4417-22. https://doi.org/10.1021/jo00301a038
26. Kawamura F, Tayano T, Satoh Y, Hara S. Suzuki A. The Michael-type reaction of B-iodo- 9-BBN/Ethoxyethyne adduct to α,β-unsaturated ketones. A selective synthesis of δ-keto esters. Chem Lett1989;18:1723–6. https://doi.org/10.1246/cl.1989.1723
27. Ochiai M, Ukita T, Iwaki S, Nagao Y, Fujita E. Oxidative grob fragmentation of gamma. - tributylstannyl alcohols with a combination of iodosylbenzene, dicyclohexylcarbodiimide, and boron trifluoride. J Org Chem 1989;54:4832–40,
28. Rahman SS, Wakefield BJ, Roberts SM, Dowle MD. Intramolecular nucleophilic addition to photochemically generated ketenes as a versatile route to lactones and lactams; synthesis of a mosquito pheromone, goniothalamin, argentilactone, and the Streptomyces L-factor. J Chem Soc Chem Commun 1989;5,303–4. https://doi.org/10.1039/C39890000303
29. Kang SK, Cho IH. An enantiospecific synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide,the mosquito oviposition attractant pheromone. Tetrahedron Lett 1989;30:743–6. https://doi.org/10.1016/S0040-4039(01)80298-7
30. Kamatani T, Tsubuki M, Tatsuzaki Y, Honda T, Heterocycles 1988;27:2107–10. Zhou W, Cheng J, Lin G. Huaxue Xuebao 1988;46:274–80.
31. Lin G, Jiang Y, Guo G, Xia K. Huaxue Xuebao 1987;45:602–5.
32. Hwang YS, Mulla MS, Chaney JD, Lin GG, Xu HJ. Attractancy and species specificity of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone. J Chem Ecol 1987;13:245–52. https://doi.org/10.1007/bf01025885
33. Barua NC, Schmidt RR. Stereoselective synthesis of the major component of a mosquito oviposition attractant pheromone from a β-lithiopropionate equivalent. Tetrahedron 1986;42:4471–4. https://doi.org/10.1016/S0040-4020(01)87287-2
34. Jefford CW, Jaggi D, Boukouvalas J. A short stereo divergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone. Tetrahedron Lett. 1986;27:4011–4. https://doi.org/10.1016/S0040-4039(00)84897-2
35. Ko KY, Eliel EL. Asymmetric synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide, the major component of the oviposition attractant pheromone of the mosquito Culex pipiens fatigans, and two of its stereoisomers. J Org Chem 1986;51:5353–62. https://doi.org/10.1016/S0040-4039(00)84897-2
36. Laurence BR, Mori K, Otsuka T, Pickett JA, Wadhams LJ. Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide. J Chem Ecol 1985;11: 643–8. https://doi.org/10.1007/bf00988573
37. Machiya K, Ichimoto I, Kirihata M, Ueda H. A convenient synthesis of four stereoisomersof 6-Acetoxy-5-hexadecanolide, the major component of the mosquito oviposition attractant pheromone. Agric Biol Chem 1985;49: 643–9. https://doi.org/10.1080/00021369.1985.108 66769
38. Ochiai M, Ukita T, Nagao Y, Fujita E. Stereochemistry of an oxidative 1,4-fragmentation of γ-stannylalcohols with a hypervalent organoiodine compound and the synthesis of erythro-6- acetoxyhexadecan-5-olide. J Chem Soc Chem Commun 1985;10:637–8. https://doi.org/10.1039 /C39850000637
39. Qiang LG, Jian XH, Chi WB, Zhong GG, Shan ZW. Studies on the identification and syntheses of insect pheromones XXI stereoselective synthesis of all the possible optical isomers of the mosquito oviposition attractant pheromone. Tetrahedron Lett 1985;26:1233 6. https://doi.org/10.1016/S0040-4039(00)98441-7
40. Yamaguchi M, Hirao I. A novel alkynylation reaction of epoxy alcohols: use in the synthesis of erythro-6-acetoxyhexadecan-5-olide. J Chem Soc Chem Commun 1984;3: 202–3. https://doi.org/10.1039/C39840000202
41. Srihari P, Kumar BP, Subbarayudu K, Yadav JS. A convergent approach for the total synthesis of (−)-synrotolide diacetate. Tetrahedron Lett 2007;48:6977-81. https://doi.org/10.1016/j.tetlet.2007.07.172
42. Jin YH, Liu P, Wang J, Baker R, Huggins J, Chu CK. Practical synthesis of D- and L-2- cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against Orthopox Viruses (Smallpox, Monkeypox, and Cowpox Virus). J Org Chem 2003;68:9012-8. https://doi.org/10.1021/jo034999v
43. Argyropoulos GN, Panagiotidis DT, Gallos KJ. Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from D-ribose. Tetrahedron: Asymmetry 2006;17:829–36. https://doi.org /10.1016/j.tetasy.2006.02.006
44. Hu TS, Yu Q, Wu YL, Wu Y. Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. J Org Chem 2001;66:853-61. https://doi.org/10.1021/jo005643b
45. Gravier-Pelletier C, Saniere M, Charvet I, Merrer YL, Depezay JC. Synthesis of (-)-Muricatacin and (-)-(5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone, from D-isoascorbic acid. Tetrahedron Lett 1994;35:115–8. https://doi.org/10.1016/0040-4039(94)88177-4
2. Grubbs RH. Olefin metathesis. Tetrahedron 2004;60:7117-40. https://doi.org/10.1016/j. tet.2004.05.124
3. Furstner A. Recent Advancements in ring closing Olefin Metathesis. Top Catal
1997;4:285-99. https://doi.org/10.1023/A:1019117012154
4. Otieno WA, Onyango TO, Pile MM, Laurence BR, Dawson GW, Wadhams LJ, Pickett JA. A field trial of the synthetic oviposition pheromone with Culex quinquefasciatus say (Diptera: Culicidae) in Kenya. Bull. Entomol. Res. 1988;78:463-70. https://doi.org/10.1017/S000748 5300013213
5. Dawson GW, Laurence BR, Pickett JA, Pile MM, Wadhams LJ. A note on the mosquito oviposition pheromone. Pestic. Sci. 1989;27:277-80. https://doi.org/10.1002/ps.2780270307
6. Blackwell A, Mordue (Luntz) AJ, Hansson BS, Wadhams LJ, Pickett JAA, A behavioural and electrophysiological study of ovi position cues for Culex quinquefasciatus. Physiol Entomol 1993;18:343-8. https://doi.org/10.1111/j.1365-3032.1993.tb00607.x
7. Fuganti C, Grasselli P, Servi SJ. Synthesis of the two enantiomeric forms of erythro-6-acetoxy-5- hexadecanolide, the major component of a mosquito oviposition attractant pheromone. J Chem Soc. Chem. Commun. 1982; 8:1285–6. https://doi.org/10.1039/C39820001285
8. Park Y, Tae J, Facile synthesis of (-)-6-Acetoxy-5-hexadecanolide by organocatalytic α- oxygenation-allylation-RCM Strategy. Synthesis 2010;21:3627–30. https://doi.org/10.1055/s-0030-1258248
9. Singh S, Guiry PJ, A facile synthesis of both enantiomers of 6-acetoxy-5-hexadecanolide, a major component of mosquito oviposition attractant pheromones. Eur. J. Org. Chem. 2009;12: 1896-1901. https://doi.org/10.1002/ejoc.200801134
10. Quinn KJ, Curto JM, McGrath KP, Biddick NA. Facile synthesis of (−)-6-acetoxy-5- hexadecanolide by size-selective ring-closing/cross metathesis. Tetrahedron Lett 2009;50: 7121–7123. https://doi.org/10.1016/j.tetlet.2009.09.179
11. Prasad KR, Anbarasan P. Stereoselective synthesis of (−)-6-acetoxyhexadecanolide: a mosquito oviposition attractant pheromone. Tetrahedron: Asymmetry 2007;18:2479–83. https://doi.org/ 10.1016/j.tetasy.2007.10.006
12. Ikishima H, Sekiguchi Y, Ichikawa Y, Kotsuki H. Synthesis of (−)-(5R,6S)-6- acetoxyhexadecanolide based on L-proline-catalyzed asymmetric aldol reactions Tetrahedron, 2006;62:311–6. https://doi.org/10.1016/j.tet.2005.08.111
13. Das S, Mishra AK, Kumar A, Ghamdi AAKA, Yadav JS. Facile total synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide from carbohydrate, a mosquito oviposition attractant pheromone. Carbohydr. Res. 2012;358:7-11. https://doi.org/10.1016/j.carres.2012.05.009
14. Dhotare B, Goswami D, Chattopadhyay A. (R)-2,3-Cyclohexylideneglyceraldehyde, a novel template for stereoselective preparation of functionalized δ-lactones: synthesis of mosquito oviposition pheromone. Tetrahedron Lett 2005;46:6219-21. https://doi.org/10.1016/j.tetlet. 2005. 07.063
15. Sun B, Peng L, Chen X, Li Y, Yamasaki K. Synthesis of (−)-(5R,6S)-6-acetoxyhexadecan-5-olide by L-proline-catalyzed asymmetric aldol reactions. Tetrahedron: Asymmetry 2005;16:1305-7. https://doi.org/10.1016/j.tetasy.2005.02.017
16. Gao X, Hall DG. 3-Boronoacrolein as an Exceptional Heterodiene in the Highly Enantio-and Diastereoselective Cr(III)-Catalyzed Three-Component [4+2]/Allylboration. J Am Chem Soc 2003;125:9308–9. https://doi.org/10.1021/ja036368o
17. Gallos JK, Mihelakis DS, Dellios CC, Pozarentzi ME. Heterocycles. 2000;53:703–707, Couladouros EA, Mihou AP. A general synthetic route towards γ- and δ-lactones. Total asymmetric synthesis of (−)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide. Tetrahedron Lett 1999;40: 4861–2. https://doi.org/10.1016/S0040-4039(99)00895-3
18. Lohray BB, Venkateswarlu S. Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone. Tetrahedron: Asymmetry 1997;8: 633–8.https://doi.org/10.1016/S0957-4166(97)00011-6
19. Carlo B, Checconi M, Righi G, Rossi L. Enantio and stereoselective synthesis of (5R,6S )-6- acetoxy- hexadecanolide, a Mosquito Oviposition attractant pheromone. Tetrahedron 1995;51: 4111–6. https://doi.org/10.1016/0040-4020(95)00128-U
20. Gravier-Pelletier C, Le Merrer Y, Depezay JC. Enantiopure hydroxylactones from L- ascorbic and D-isoascorbic acids. Part II. Synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide and its diastereomers. Tetrahedron 1995;51:1663–74. https://doi.org/10.1016/0040-4020(94)01033-V
21. Coutrot P, Bomont CG. 5-formyl-δ—valerolactone: A useful synthon for the chiralsynthesis of the vespa orientalis pheromone and the mosquito oviposition attractant pheromone. Tetrahedron Lett 1994;35:8381–4. https://doi.org/10.1016/S0040-4039(00)74412-1
22. Ramaswamy S, Oehlschlager AC. Chemico-microbial syntheses of Japanese beetle and mosquito oviposition pheromones. Tetrahedron 1991;47:1145–56. https://doi.org/10.1016/S0040-4020(01) 86371-7
23. Wu W, Wu YJ. A concise synthesis of the natural mosquito Oviposition attractant pheromone from D-Glucose. Carbohydr. Chem. 1991;10:279–81. https://doi.org/10.1080/ 07328309108543907
24. Wang ZM, Qian XH, Zhou WS. Stereoselective synthesis of (-)-(5R,6S)-6-acetoxy-5- hexadecanolide, the mosquito oviposition attractant pheromone. Tetrahedron 1990;46:1191–6. https://doi.org/10.1016/S0040-4020(01)86684-9
25. Kotsuki H, Kadota I, Ochi M. A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor. J Org Chem 1990;55:4417-22. https://doi.org/10.1021/jo00301a038
26. Kawamura F, Tayano T, Satoh Y, Hara S. Suzuki A. The Michael-type reaction of B-iodo- 9-BBN/Ethoxyethyne adduct to α,β-unsaturated ketones. A selective synthesis of δ-keto esters. Chem Lett1989;18:1723–6. https://doi.org/10.1246/cl.1989.1723
27. Ochiai M, Ukita T, Iwaki S, Nagao Y, Fujita E. Oxidative grob fragmentation of gamma. - tributylstannyl alcohols with a combination of iodosylbenzene, dicyclohexylcarbodiimide, and boron trifluoride. J Org Chem 1989;54:4832–40,
28. Rahman SS, Wakefield BJ, Roberts SM, Dowle MD. Intramolecular nucleophilic addition to photochemically generated ketenes as a versatile route to lactones and lactams; synthesis of a mosquito pheromone, goniothalamin, argentilactone, and the Streptomyces L-factor. J Chem Soc Chem Commun 1989;5,303–4. https://doi.org/10.1039/C39890000303
29. Kang SK, Cho IH. An enantiospecific synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide,the mosquito oviposition attractant pheromone. Tetrahedron Lett 1989;30:743–6. https://doi.org/10.1016/S0040-4039(01)80298-7
30. Kamatani T, Tsubuki M, Tatsuzaki Y, Honda T, Heterocycles 1988;27:2107–10. Zhou W, Cheng J, Lin G. Huaxue Xuebao 1988;46:274–80.
31. Lin G, Jiang Y, Guo G, Xia K. Huaxue Xuebao 1987;45:602–5.
32. Hwang YS, Mulla MS, Chaney JD, Lin GG, Xu HJ. Attractancy and species specificity of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone. J Chem Ecol 1987;13:245–52. https://doi.org/10.1007/bf01025885
33. Barua NC, Schmidt RR. Stereoselective synthesis of the major component of a mosquito oviposition attractant pheromone from a β-lithiopropionate equivalent. Tetrahedron 1986;42:4471–4. https://doi.org/10.1016/S0040-4020(01)87287-2
34. Jefford CW, Jaggi D, Boukouvalas J. A short stereo divergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone. Tetrahedron Lett. 1986;27:4011–4. https://doi.org/10.1016/S0040-4039(00)84897-2
35. Ko KY, Eliel EL. Asymmetric synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide, the major component of the oviposition attractant pheromone of the mosquito Culex pipiens fatigans, and two of its stereoisomers. J Org Chem 1986;51:5353–62. https://doi.org/10.1016/S0040-4039(00)84897-2
36. Laurence BR, Mori K, Otsuka T, Pickett JA, Wadhams LJ. Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide. J Chem Ecol 1985;11: 643–8. https://doi.org/10.1007/bf00988573
37. Machiya K, Ichimoto I, Kirihata M, Ueda H. A convenient synthesis of four stereoisomersof 6-Acetoxy-5-hexadecanolide, the major component of the mosquito oviposition attractant pheromone. Agric Biol Chem 1985;49: 643–9. https://doi.org/10.1080/00021369.1985.108 66769
38. Ochiai M, Ukita T, Nagao Y, Fujita E. Stereochemistry of an oxidative 1,4-fragmentation of γ-stannylalcohols with a hypervalent organoiodine compound and the synthesis of erythro-6- acetoxyhexadecan-5-olide. J Chem Soc Chem Commun 1985;10:637–8. https://doi.org/10.1039 /C39850000637
39. Qiang LG, Jian XH, Chi WB, Zhong GG, Shan ZW. Studies on the identification and syntheses of insect pheromones XXI stereoselective synthesis of all the possible optical isomers of the mosquito oviposition attractant pheromone. Tetrahedron Lett 1985;26:1233 6. https://doi.org/10.1016/S0040-4039(00)98441-7
40. Yamaguchi M, Hirao I. A novel alkynylation reaction of epoxy alcohols: use in the synthesis of erythro-6-acetoxyhexadecan-5-olide. J Chem Soc Chem Commun 1984;3: 202–3. https://doi.org/10.1039/C39840000202
41. Srihari P, Kumar BP, Subbarayudu K, Yadav JS. A convergent approach for the total synthesis of (−)-synrotolide diacetate. Tetrahedron Lett 2007;48:6977-81. https://doi.org/10.1016/j.tetlet.2007.07.172
42. Jin YH, Liu P, Wang J, Baker R, Huggins J, Chu CK. Practical synthesis of D- and L-2- cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against Orthopox Viruses (Smallpox, Monkeypox, and Cowpox Virus). J Org Chem 2003;68:9012-8. https://doi.org/10.1021/jo034999v
43. Argyropoulos GN, Panagiotidis DT, Gallos KJ. Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from D-ribose. Tetrahedron: Asymmetry 2006;17:829–36. https://doi.org /10.1016/j.tetasy.2006.02.006
44. Hu TS, Yu Q, Wu YL, Wu Y. Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. J Org Chem 2001;66:853-61. https://doi.org/10.1021/jo005643b
45. Gravier-Pelletier C, Saniere M, Charvet I, Merrer YL, Depezay JC. Synthesis of (-)-Muricatacin and (-)-(5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone, from D-isoascorbic acid. Tetrahedron Lett 1994;35:115–8. https://doi.org/10.1016/0040-4039(94)88177-4
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Oct 8, 2020
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Garikipati Karuna Deepthi, Banoth Reddy, Mandava Bhuvan Tej, P Rasvan Khan, & Mandava Venkata Basaveswara Rao. (2020). SYNTHESIS OF (-)-(5R, 6S)-6-ACETOXY-5-HEXADECANOLIDE A PHEROMONE. Journal of Population Therapeutics and Clinical Pharmacology, 27(4), 118-125. https://doi.org/10.53555/gys1z388
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Author Biographies
Garikipati Karuna Deepthi
Department of Chemistry, Krishna University, Rudravaram, Andhra Pradesh, 521003, India
Banoth Reddy
Department of Chemistry, Krishna University, Rudravaram, Andhra Pradesh, 521003, India
Mandava Bhuvan Tej
Koneru Lakshmaiah Education Foundation (Deemed to be University), Vaddeswaram, Andhra Pradesh, 522302, India.
P Rasvan Khan
Koneru Lakshmaiah Education Foundation (Deemed to be University), Vaddeswaram, Andhra Pradesh, 522302, India.
Mandava Venkata Basaveswara Rao
Department of Chemistry, Krishna University, Rudravaram, Andhra Pradesh, 521003, India
How to Cite
Garikipati Karuna Deepthi, Banoth Reddy, Mandava Bhuvan Tej, P Rasvan Khan, & Mandava Venkata Basaveswara Rao. (2020). SYNTHESIS OF (-)-(5R, 6S)-6-ACETOXY-5-HEXADECANOLIDE A PHEROMONE. Journal of Population Therapeutics and Clinical Pharmacology, 27(4), 118-125. https://doi.org/10.53555/gys1z388