Asymmetric total synthesis of the Caribbean fruit fly pheromone (+)-epianastrephin

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5626-5630

  Schultz, Arthur G ^a   Kirincich, Steven J ^a  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPIANASTREPHIN; PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE;

EID: 0029766110     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960568j     Document Type: Article

References (27)

1. For a current review of the chemistry of fruit flies, see: Fletcher, M. T.; Kitching, W. Chem. Rev. 1995, 95, 789-828.
2. (a) Nation, J. L. Ann. Entomol. Soc. Am. 1972, 65, 1364.
3. (b) Perdemo, A. J.; Nation, J. L.; Baronowski, R. M. Environm. Entomol. 1976, 5, 1208.
4. For the earlier isolation of anastrephin and epianastrephin from the Mexican fruit fly (A. ludens), see: Gaxiola, R. E. Thesis, Technical University of Monterrey, Mexico, 1975.
5. Stokes, J. B.; Uebel, E. C.; Warthen, J. D., Jr.; Jacobsen, M.; Flippen-Anderson, J. L.; Gilardi, R.; Spishakoff, L. M.; Wilzer, K. R. J. Agric. Food Chem. 1983, 31, 1162-1167.
6. Battiste, M. A.; Strekowski, L.; Vanderbilt, D. P.; Visnick, M.; King, R. W.; Nation, J. L. Tetrahedron Lett. 1983, 24, 2611-2614 and references cited therein.
7. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
8. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
9. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
10. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
11. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
12. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
13. For additional syntheses of anastrephin and epianastephin, see: (a) Visnick, M. Ph.D. Dissertation, University of Florida, 1983. (b) Strekowski, L.; Visnick, M.; Battiste, M. A. J. Org. Chem. 1986, 51, 4836-4839. (c) Saito, A.; Matsushita, H.; Kaneko, H. Chem. Lett. 1984, 729-730. (d) For a recent report of the stereoselective rearrangement of suspensolide to bicyclic lactones, see: Battiste, M. A.; Strekowski, L.; Coxon, J. M.; Wydra, R. L.; Harden, D. B. Tetrahedron Lett. 1991, 32, 5303-5304. (e) Mori, K.; Nakazono, Y. Liebigs Ann. Chem. 1988, 167-174. (f) For the first enantioselective syntheses of (-)-anastrephin and (-)-epianastrephin, see: Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266-6279. (g) Irie, O.; Shishido, K. Chem. Lett. 1995, 53-54.
14. (a) 3,4-Dihydro-5-methyl-2(1H)-benzopyran-1-one has been prepared in 77% overall yield from o-tolylacetic acid; see: Schultz, A. G.; Kirincich, S. J. J. Org. Chem. 1996, 61, 5631-5634.
15. (b) For the first preparation of 3,4-Dihydro-5-methyl-2(1H)-benzopyran-1-one, see: Bhide, B. H.; Shah, K. K. Ind. J. Chem. 1980, 19b, 9-12.
16. Schultz, A. G.; Green, N. J. J. Am. Chem. Soc. 1991, 113, 4931-4936.
17. Birch reduction-methylation of the 2,3-dimethylbenzamide corresponding to 2 gave little if any diastereoselectivity (unpublished observations of S. J. Kirincich); the same process with the 2-methyl-benzamide gave a diastereomer distribution >99:1. Aggregation effects may play a significant role in the stereoselectivity of these and related alkylations as noted earlier: Schultz, A. G.; Macielag, M.; Sundararaman, P.; Taveras, A. G.; Welch, M. J. Am. Chem. Soc. 1988, 110, 7828-7841.
18. Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1993, 115, 7904-7905.
19. Schultz, A. G.; Hoglen, D. K.; Holoboski, M. A. Tetrahedron Lett. 1992, 33, 6611-6614.
20. King, S. A. J. Org. Chem. 1994, 59, 2253-2256.
21. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
22. (a) Chuang, C.-P.; Gallucci, J. C.; Hart, D. J. J. Org. Chem. 1988, 53, 3210-3218.
23. (b) Keck, G. E.; Yates, J. B. J. Org. Chem. 1982, 47, 3590-3591.
24. (c) Coblens, K. E.; Muralidharan, V. B.; Ganem, B. J. Org. Chem. 1982, 47, 5041-5042.
25. It has been suggested that the stereoselectivities observed in ref 14 may be the result of a stereoelectronic effect that involves stabilization of an equatorial radical by the nonbonding orbital of the oxygen atom in the lactone bridge; see: Ramaiah, M. Tetrahedron 1987, 43, 3541-3676.
26. Greenwald, R.; Chaykovsky, M.; Corey, E. J. J. Org. Chem. 1983, 28, 1128-1129.
27. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.