Total synthesis of (-)-hennoxazole A [17]

Journal of the American Chemical Society

Volumn 121, Issue 20, 1999, Pages 4924-4925

  Williams, David R ^a   Brooks, Dawn A ^a   Berliner, Martin A ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HENNOXAZOLE A; NATURAL PRODUCT; UNCLASSIFIED DRUG;

DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HYDROGENATION; LETTER; MARINE ENVIRONMENT; NONHUMAN; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033606291     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9904686     Document Type: Letter

References (35)

1. (a) Faulker, D. J. Nat. Prod. Rep. 1993, 10, 497; 1994, 11, 395; 1995, 12, 135; 1996, 13, 435.
2. (a) Faulker, D. J. Nat. Prod. Rep. 1993, 10, 497; 1994, 11, 395; 1995, 12, 135; 1996, 13, 435.
3. (a) Faulker, D. J. Nat. Prod. Rep. 1993, 10, 497; 1994, 11, 395; 1995, 12, 135; 1996, 13, 435.
4. (a) Faulker, D. J. Nat. Prod. Rep. 1993, 10, 497; 1994, 11, 395; 1995, 12, 135; 1996, 13, 435.
5. (b) Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753.
6. (a) Ichiba, T.; Yoshida, W.; Scheuer, P.; Higa, T. J. Am. Chem. Soc. 1991, 113, 3173.
7. (b) Higa, T.; Tanaka, J.; Kitamura, A.; Koyama, T.; Takahashi, M.; Uchida, T. Pure Appl. Chem. 1994, 66, 2227.
8. (a) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558.
9. (b) Wipf, P.; Lim, S. Chimia 1996, 50, 157. We thank Professor Wipf for proton and carbon NMR spectra of authentic hennoxazole A for our comparisons.
10. Binns, F.; Roberts, S. M.; Taylor, A.; Williams, C. F. J. Chem. Soc., Perkin Trans. 1 1993, 899.
11. No evidence for the formation of an intermediate fluoride was observed, and fluoride-induced desilylation was not encountered. Lafargue, P.; Guenot, P.; Lellouche, J.-P. Heterocycles 1995, 41, 947.
12. Williams, D. R.; Lowder, P. D.; Gu, Y.-G.; Brooks, D. A. Tetrahedron Lett. 1997, 58, 331.
13. Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Pagel, M. Tetrahedron Lett. 1998, 39, 8023.
14. Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251.
15. Corey, E. J.; Yu, C-M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495.
16. 2; -78 °C) produced a mixture of alcohols (40: 60 ratio) favoring the corresponding C8 (S)-isomer.
17. Nishiyama, H.; Yokoyama, H.; Harimatsu, S.; Itoh, K. Tetrahedron Lett. 1982, 23, 1267.
18. 4 (for Mosher ester analysis of 11; see Supporting Information). Seebach, D. Synthesis 1969, 17. Braun, M.; Seeback, D. Chem. Ber. 1976, 109, 669.
19. 4 (for Mosher ester analysis of 11; see Supporting Information). Seebach, D. Synthesis 1969, 17. Braun, M.; Seeback, D. Chem. Ber. 1976, 109, 669.
20. 3 quench to prevent hydrolysis of the 1,3-dithiane.
21. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287.
22. (a) Minato, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766.
23. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
24. (a) Terashima, S.; Tanno, N.; Koga, K. J. Chem Soc. Chem. Commun. 1980, 1026.
25. (b) Terashima, S.; Tanno, N.; Koga, K. Chem Lett. 1980, 981.
26. 4, super hydride) or (-)-N-methylephedrine provided selectivity slightly favoring the undesired (S)-isomer. Interestingly, our Terashima reduction ((+)-N-methylephedrine) of the corresponding (S)-methyl ether (C8) of ketone 16 gave predominantly the all-syn arrangement (ratio > 20:1).
27. For leading advances in the synthesis of 1,3,5-polyols: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753.
28. (b) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058.
29. Abbott Laboratories generously supplied us with quantities of (S)-3-butyn-2-ol resulting from enzymatic lipase resolution. The alkyne was converted to (2S,3Z)-3-penten-2-ol by methylation and Lindlar hydrogenation. Alkylation with methallyl chloride (NaH) afforded the substrate for Wittig rearrangement.
30. Midland, M.-M.; Tsai, D. J.-S. J. Am. Chem. Soc. 1985, 107, 3915. Review: Mikami, K.; Nakai, T. Synthesis 1991, 594.
31. Midland, M.-M.; Tsai, D. J.-S. J. Am. Chem. Soc. 1985, 107, 3915. Review: Mikami, K.; Nakai, T. Synthesis 1991, 594.
32. Eastwood, F. W.; Harrington, K. J.; Josan, J. S.; Pura, J. L. Tetrahedron Lett. 1970, 5223.
33. (a) Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
34. (b) Molander, G. A.; Nichols, P. J. J. Org. Chem. 1996, 61, 6040.
35. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26.