First syntheses of (-)-tauranin and antibiotic (-)-BE-40644 based on lipase-catalyzed optical resolution of albicanol.
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.
Ishii
Sadayuki
S
Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Chiba 247-8510, Japan.
Fujii
Mikio
M
Akita
Hiroyuki
H
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D055162:Biocatalysis; D008049:Lipase / Q000378:metabolism*; D009281:Naphthalenes / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C095251:BE 40644; D016227:Benzoquinones; D009281:Naphthalenes; D011809:Quinones; D012717:Sesquiterpenes; C528158:tauranin; C438910:albicanol; D008049:Lipase