First syntheses of (-)-tauranin and antibiotic (-)-BE-40644 based on lipase-catalyzed optical resolution of albicanol.

Abstract

First syntheses of sesquiterpene quinones (-)-tauranin and (-)-BE-40644 which exhibited strong cytotoxicity against several cancer cell lines, were achieved from (8aS)-albicanol obtained by enzymatic optical resolution. By comparison of the sign of specific rotation between synthetic (12bS)-BE-40644 and natural (-)-BE-40644, the absolute configurations of natural (-)-BE-40644 were determined to be 4aS, 6aS, 12aR, 12bS.

• Authors: Sadayuki Ishii, Mikio Fujii, Hiroyuki Akita
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 57 Issue 10 Pg. 1103-6 (Oct 2009) ISSN: 1347-5223 [Electronic] Japan
• PMID: 19801866 (Publication Type: Journal Article)

Chemical References

• BE 40644
• Benzoquinones
• Naphthalenes
• Quinones
• Sesquiterpenes
• tauranin
• albicanol
• Lipase

Topics

• Benzoquinones (chemical synthesis, chemistry)
• Biocatalysis
• Lipase (metabolism)
• Naphthalenes (chemistry)
• Quinones (chemical synthesis, chemistry)
• Sesquiterpenes (chemical synthesis, chemistry)
• Stereoisomerism