Abstract

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

中文翻译：

---

抗生素大乳素S的全合成研究：合成C1-C9和C10-C24片段的常规方法

摘要

通过以下方法合成了24元多烯大环内酯大环内酯S的C1-C9和C10-C24节段：环氧化物-开环反应，Ohira-Bestmann炔烃形成，螯合控制的亲核加成反应以及Still- Gennari烯烃化是关键步骤。从容易获得的葡萄糖二丙酮化物开始，采用卡隆方法合成关键中间体，并采用收敛方法合成关键C10–C24片段。

通过以下方法合成了24元多烯大环内酯大环内酯S的C1-C9和C10-C24节段：环氧化物-开环反应，Ohira-Bestmann炔烃形成，螯合控制的亲核加成反应以及Still- Gennari烯烃化是关键步骤。从容易获得的葡萄糖二丙酮化物开始，采用卡隆方法合成关键中间体，并采用收敛方法合成关键C10–C24片段。