Towards the total synthesis of aurodox: Preparation of the key hemiacetal-lactone

TETRAHEDRON LETTERS

卷:66

Article

Ohara, Motoyoshi¹  Ikeda, Akari^1,2  Nakajima, Asuka¹  Ono, Takanori¹  Noguchi, Yoshihiko^1,2  Watanabe, Akito¹  Hirose, Tomoyasu^1,2  Sunazuka, Toshiaki^1,2 

[1] Kitasato Univ, Grad Sch Infect Control Sci, Minato Ku, 5-9-1 Shirokane, Tokyo 1088641, Japan

[2] Kitasato Univ, Omura Satoshi Mem Inst, Minato Ku, 5-9-1 Shirokane, Tokyo 1088641, Japan

关键词: Aurodox;    Type III secretion system inhibitor;    Wittig reaction/Horner-Wadsworth-Emmons reaction;    Stereoselective epoxidation;    Aldol reaction;   

DOI  :  10.1016/j.tetlet.2020.152799

来源: Elsevier

【 摘 要 】

We describe the preparation of a cyclic hemiacetal-lactone 6, which is a key intermediate in the total synthesis of Aurodox (1) and also a degradation product of aurodox. The bicyclic core of 6 was obtained by lactonization and hemiacetalization after stereo-selective epoxidation at late stage. The construction of olefins utilized a Wittig reaction and a Horner-Wadsworth-Emmons reaction using D-pantolactone (14). (C) 2020 Published by Elsevier Ltd.

【 授权许可】

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