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Paper | Special issue | Vol 97, No. 1, 2018, pp.283-291
Published online, 9th February, 2018
DOI: 10.3987/COM-18-S(T)18
Stereoselective Synthesis of a Pivotal Chiral Intermediate for Natural Salicylic Macrolides

Yoshihito Oguma, Nozomi Yamamoto, Kenji Sugimoto, and Yuji Matsuya*

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

Abstract

As a part of our ongoing research projects on the synthesis of natural salicylic macrolides, the optically active protected salicylate bearing the chiral diene substituent was required as a pivotal synthetic intermediate. The synthesis of the compound was achieved with a high optical purity starting from D-mannitol through Heck coupling reaction and terminal methylenation as key C–C bond forming reactions.