Determination of the Absolute Stereochemistry of (-)-Galbonolide A

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3230-3235

  Tse, Bruno ^a   Blazey, Charles M ^a   Tu, Ben ^a   Balkovec, James ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

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[No Author keywords available]

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EID: 1542629718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (11)

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.
4. Tse, B. J. Am. Chem. Soc. 1996, 118, 7094.
5. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
6. Since the goal was to convert 18 to 17 regardless of the yield, no effort to optimize the ratio of 19:20 was carried out.
7. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194.
8. Ladner, W. Chem. Ber. 1983, 116, 3413.
9. d's (Scheme 6) confirmed the configuration of 25. The diastereoselectivity of the contrasteric attack of the lithium enolate of 24 on allyl bromide was 12:1.
10. 2 and pyridine-water mixture and were characterized by Dr. Mark Greenlee and Ms. Regina Black of this department. Both epi compounds have also been reported in the literature, e.g., see ref 3.
11. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.