Total synthesis of (-)-galbonolide B and the determination of its absolute stereochemistry

Journal of the American Chemical Society

Volumn 118, Issue 30, 1996, Pages 7094-7100

  Tse, Bruno ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; GALBONOLIDE B; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0029780098     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961344l     Document Type: Article

References (24)

1. Abe, Y.; Nakayama, H.; Shimazu, A.; Furihata, K.; Ikeda, K.; Furihata, K.; Seto, H.; Otake, N. J. Antibiot. 1985, 38, 1810.
2. Achenbach, H.; Muhlenfeld, A.; Fauth, U.; Zahner, H. Tetrahedron Lett. 1985, 26, 6167.
3. Achenbach, H.; Muhlenfeld, A.; Fauth, U.; Zahner, H. Ann. N. Y. Acad. Sci. 1988, 544, 128. The speculated absolute stereochemistry was different from that shown in structure 1.
4. Unpublished results from Dr. Richard Ball of the Merck Crystallography Group in Rahway, NJ, who kindly provided the X-ray structure of galbonolide B.
5. An authentic sample of galbonolide B was kindly provided by Dr. Guy Harris of Merck Research Laboratories, Rahway, NJ.
6. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
7. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
8. Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 1839.
9. Janout, V.; Regen, S. L. J. Org. Chem. 1982, 47, 3331.
10. 3, whereas the latter showed up at 2.17 ppm.
11. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
12. b. equation presented
13. If the bromide was not first displaced by iodide, reaction with lithiated ethyl vinyl ether was low-yielding.
14. For example, see: Baldwin, J. E.; Hofle, G. A.; Lever, O. W. J. Am. Chem. Soc. 1974, 96, 7125.
15. Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 4327.
16. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
17. The E geometry of the C6-C7 double bond of alcohol 32 was confirmed by the NOE observed between the proton on C7 and the 2H's on C5. equation presented
18. For example, see: Corey, E. J.; Niimura, K.; Konishi, Y.; Hashimoto, S.; Hamada, Y. Tetrahedron Lett. 1986, 27, 2199.
19. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194.
20. Ladner, W. Chem. Ber. 1983, 116, 3413.
21. b, and the 2 H's on C5 confirmed the structure of 26. equation presented
22. 2 or pyridine-water mixture and were characterized by Dr. Mark Greenlee and Ms. Regina Black of this department. Both compounds have also been reported in the literature, e.g., see ref 3.
23. An example of the use of 2,4,6-trimethylbenzylidene acetal as a protecting group for diols can be found in the following: Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3213.
24. Acetal 23 and it cis isomer were distinguished by NOE experiments. The latter showed a strong NOE between the benzylic proton and the proton next to the -COOMe moiety, whereas the former did not.