Asymmetric synthesis of seven-carbon segments of the phorboxazoles and (-)-discodermolide: Complementary route from racemic trans-2,4-dimethyl-8- oxabicyclo[3.2.1]oct-6-en-3-one

Tetrahedron

Volumn 55, Issue 14, 1999, Pages 4315-4324

  Misske, Andrea M ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; BENZOPHENONE DERIVATIVE; BICYCLO[3.2.1]OCTANE DERIVATIVE; BICYCLO[3.3.1]NONANE DERIVATIVE; DISCODERMOLIDE; LACTONE DERIVATIVE; NATURAL PRODUCT; OXAZOLE DERIVATIVE; PHORBOXAZOLE A; PHORBOXAZOLE B; TERT BUTYL METHYL ETHER; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; PRIORITY JOURNAL; RACEMIC MIXTURE; SPONGE (PORIFERA); STEREOCHEMISTRY; TRANS ISOMER;

EID: 0033118794     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00127-1     Document Type: Article

References (48)

1. a) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126;
2. b) Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. J. Am. Chem. Soc. 1996, 118, 9422;
3. c) Molinski, T. F. Tetrahedron Lett. 1996, 37, 7879.
4. a) Gunasekera, S. P.; Gunasekera, M.; Longley, R. E. J. Org. Chem. 1990, 55, 4912;
5. b) Gunasekera, S. P. Gunasekera, M.; Longley, R. E. J. Org. Chem. 1991, 56, 1346.
6. Hung, D. T.; Jamison, T. F.; Schreiber, S. L. Chemistry & Biology 1996, 3, 623.
7. Total synthesis: a) Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597.
8. Other synthetic efforts: b) Lee, C. S.; Forsyth, C. J. Tetrahedron Lett. 1996, 37, 6449;
9. c) Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1997, 62, 5672;
10. d) Forsyth, C. J.; Ahmed, F. Tetrahedron Lett. 1998, 39, 183;
11. e) Ye, T.; Pattenden, G. Tetrahedron Lett. 1998, 39, 319;
12. f) Pattenden, G.; Plowright, A. T.; Tornos, J. A.; Ye, T. Tetrahedron Lett. 1998, 39, 6099;
13. g) Paterson, I.; Arnott, E. A. Tetrahedron Lett. 1998, 39, 7185;
14. h) Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251;
15. i) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905.
16. Total synthesis of (-)-discodermolide: a) Nerenberg, J. B.; Hung, D. T.; Somers, P. K.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 12621;
17. b) Smith, A. B. III.; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011;
18. c) Harried, S. S.; Yang, G.; Strawn, M. A.; Myles, D. A. J. Org. Chem. 1997, 62, 6098;
19. Total synthesis of (+)-discodermolide: d) Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 11054;
20. e) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
21. Other synthetic efforts: f) Golec, J. M. C.; Jones, S. D. Tetrahedron Lett. 1993, 34, 8259;
22. g) Golec, J. M. C.; Gillespie, R. J. Tetrahedron Lett. 1993, 34, 8167;
23. h) Evans, P. L.; Golec, J. M. C.; Gillespie, R. J. Tetrahedron Lett. 1993, 34, 8163;
24. i) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 24, 1790;
25. j) Clark, D. L.; Heathcock, C. H. J. Org. Chem. 1993, 58, 5878;
26. k) Yang, G.; Myles, D. C. Tetrahedron Lett. 1994, 35, 1313;
27. l) Yang, G.; Myles, D. C. Tetrahedron Lett. 1994, 35, 2503;
28. m) Paterson, I.; Schlapbach, A. Synlett, 1995, 498;
29. n) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817.
30. a) Lampe, T. F. J.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1996, 1931;
31. b) Dunkel, R.; Mentzel, M.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 14929;
32. c) Lautens, M.; Ma, S.; Yee, A. Tetrahedron Lett. 1995, 37, 4185;
33. d) Nowakowski, M.; Hoffmann, H. M. R. Tetrahedron Lett. 1997, 38, 1001.
34. a) Hoffmann, H. M. R. Angew. Chem. Int. Ed. 1984, 23, 1;
35. b) Föhlisch, B.; Herter, R. Synthesis 1982, 976;
36. c) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344.
37. Basic equilibration (DBU, DCM or MeOH, MeONa) of 2α,4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one gave the epimers in a ratio of 2α,4α:2α,4β = 1.6:1 These were not separable by conventional means.
38. 2-promoted reduction of oxabicyclic ketone rac-2 furnishes 2α-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one rac-14, a precursor of tetrahydropyran units of spongistatin and lasonolide. (Formula Presented) For the [4+3] cycloaddition of α,α-dimethoxysilyl enol ethers to dienes see also: Pierau, S.; Hoffmann, H. M.R. Synlett, 1999, 213.
39. 2-promoted reduction of oxabicyclic ketone rac-2 furnishes 2α-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one rac-14, a precursor of tetrahydropyran units of spongistatin and lasonolide. (Formula Presented) For the [4+3] cycloaddition of α,α-dimethoxysilyl enol ethers to dienes see also: Pierau, S.; Hoffmann, H. M.R. Synlett, 1999, 213.
40. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135.
41. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
42. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448.
43. A "racemic switch" has been defined as the redevelopment in single-enantiomer form of a drug that was first approved as a racemate; see: Stinson, S. C. Chem. Eng. News 1998, September 21, 83-104. In our case the early racemic switch provides two key single-isomer precursors of structurally different bioactive natural products.
44. a) Evans, D. A.; Coleman, P. J.; Dias, C. L. Angew. Chem. Int. Ed. 1997, 36, 2738;
45. b) Evans, D. A.; Trotter, B. W.; Côté, B.; Coleman, P. J. Angew. Chem. Int. Ed. 1997, 36, 2741;
46. c) Evans, D. A.; Trotter, B. W.; Côté, B.; Coleman, P. J.; Dias, C. L.; Tyler, A. N. Angew. Chem. Int. Ed. 1997, 36, 2744;
47. d) Guo, J.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem. Int. Ed. 1998, 37, 187;
48. e) Hayward, M. M.; Roth, R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.; Kishi, Y. Angew. Chem. Int. Ed. 1998, 37, 190.