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Communication | Special issue | Vol 82, No. 2, 2010, pp.1113-1118
Published online, 17th August, 2010
DOI: 10.3987/COM-10-S(E)76
Concise Substrate-Controlled Asymmetric Total Synthesis of (+)-3-(Z)-Dihydrorhodophytin

Byungsook Kim, Te-ik Sohn, Sanghee Kim, Deukjoon Kim,* and Jongkook Lee

*The Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Shillim-Dong, San 56-1, Kwanak-Gu, Seoul 151-742, Korea

Abstract

The first asymmetric total synthesis of (+)-3-(Z)-dihydrorhodophytin (1) has been accomplished in 15 steps in 17% overall yield from readily available starting material 6 in a substrate-controlled manner. Key steps in our synthesis are a highly stereoselective dianion alkylation for the synthesis of the α,α’-anti-RCM substrate and a strategy for the introduction of the chlorine function.