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Paper | Special issue | Vol 88, No. 1, 2014, pp.441-452
Published online, 23rd July, 2013
DOI: 10.3987/COM-13-S(S)50
Highly Efficient, Enantiocontrolled Total Syntheses of (+)-Heliannuol D and (–)-Helibisabonol A

Yuki Manabe, Makoto Kanematsu, Mayu Osaka, Masahiro Yoshida, and Kozo Shishido*

*Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan

Abstract

Enantiocontrolled total syntheses of (+)-heliannuol D (1) and ()-helibisabonol A (2) have been accomplished efficiently from a common intermediate 9, derived from the optically pure aryl allyl ether 7 via a chirality transfer through a Lewis acid-mediated Claisen rearrangement and asymmetric dihydroxylation.