Volume 19, Issue 12 pp. 1245-1253
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Synthesis of (-)-herbertenediol and (aR, aS)-mastigophorenes A via asymmetric intramolecular heck coupling reaction

Ai-Min Zhang

Ai-Min Zhang

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Guo-Qiang Lin

Guo-Qiang Lin

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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First published: 26 August 2010
Citations: 4

Dedicated to Professor HUANG Wei-Yuan on the occasion of his 80th birthday.

Abstract

Total enantioselective synthesis of the natural (-)-Herbertenediol (1) was accomplished in eleven steps with an overall yield of 15% starting from the 2-methoxy-4-methyl-phenol. The total synthesis features asymmetric intramolecular Heck reaction and Wolff-Kishner-Huang reduction. (aR, aS)-Mastigophorenes A was also synthesized through the oxidative coupling reaction.

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