Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Papers
Improved Syntheses of Morinol C and D by Employing Mizoroki-Heck Reaction and Their Cytotoxic and Antimicrobial Activities
Koji OGURATakuya SUGAHARAMasafumi MARUYAMAKoichi AKIYAMASatoshi YAMAUCHI
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2010 Volume 74 Issue 8 Pages 1641-1644

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Abstract

Improved syntheses of optically pure (−)- and (+)-morinol C, and (−)- and (+)-morinol D were achieved by employing the Mizoroki-Heck reaction to construct the cinnamyl moiety. The protective group of the alkene substrate affected the yield of this key reaction. The reaction with a combination of the acetate-protected olefin and 4-methoxyphenylboronic acid gave the best result producing morinol C and D. All stereoisomers of morinol C and D showed cytotoxic activity, with (R,R)-morinol C showing the highest antibacterial activity.

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© 2010 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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