氯甾三烯糖的全合成。

Takahashi Shunya, Hama Takenori, Nogawa Toshihiko, Ogawa Narihito, Koshino Hiroyuki

RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan.

Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki 214-8571, Japan.

ACS Omega. 2023 Sep 11;8(38):35382-35392. doi: 10.1021/acsomega.3c05277. eCollection 2023 Sep 26.

This paper considers the total synthesis of a cellular differentiation regulator of , clostrienose, which is a unique fatty-acid glycosyl ester consisting of clostrienoic acid, (3,5,8,10)-3-hydroxy-tetradeca-5,8,10-trienoic acid and α-d-galactofuranosyl-(1 → 2)-α-l-rhamnose. The key features of our synthesis include stereoselective construction of a skipped-triene system in clostrienoic acid and its esterification with a disaccharide residue. The partially protected clostrienoic acid employed for the coupling also served for the preparation of l-rhamnosyl clostrienoate, thus leading to confirmation of the proposed structure unambiguously.

本文研究了细胞分化调节剂梭链孢酸的全合成，梭链孢酸是一种独特的脂肪酸糖基酯，由梭链孢烯酸、(3,5,8,10)-3-羟基-十四碳-5,8,10-三烯酸和α-D-呋喃半乳糖基-(1→2)-α-L-鼠李糖组成。我们合成的关键特征包括在梭链孢烯酸中立体选择性构建一个跳跃三烯系统及其与二糖残基的酯化反应。用于偶联的部分保护的梭链孢烯酸也用于制备鼠李糖基梭链孢烯酸酯，从而明确证实了所提出的结构。