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Short Paper | Regular issue | Vol 100, No. 1, 2020, pp.137-144
Published online, 30th August, 2019
DOI: 10.3987/COM-19-14120
An Improved Synthesis of a Salicylated Divinylcarbinol Derivative as a Part of Salicylic Macrolides

Aki Kohyama, Yoshihito Oguma, Takumi Yamagishi, Kenji Sugimoto, and Yuji Matsuya*

*Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan

Abstract

An improved enantioselective synthesis of (R)-salicylated divinyl carbinol derivative (4), the key intermediate for the total synthesis of natural salicyclic macrolides, has been achieved. Key steps of the synthesis involve the introduction of the chirality by reliable Sharpless asymmetric epoxidation, carbon-carbon bond formation via Heck reaction and the regeneration of a terminal alkene structure via deoxygenation. The efficient route shortened the reaction sequence and enabled the preparation of (R)-4 in 4 steps in 28% overall yield from divinyl carbinol.