基于手性三环亚胺内酰胺的鞘氨醇真菌素 F 的全合成。

Total synthesis of sphingofungin F based on chiral tricyclic iminolactone.

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PRC.

出版信息

J Org Chem. 2010 Apr 16;75(8):2737-40. doi: 10.1021/jo100183d.

DOI:10.1021/jo100183d

PMID:20329736

Abstract

A new, efficient synthesis of sphingofungin F has been accomplished with 10.4% overall yield in 15 steps. The salient features of the synthesis are the utilization of methyl tricyclic iminolactone 3 for the asymmetric aldol reaction as a key step to introduce two desired stereogenic centers, one-pot reaction for the synthesis of omega-hydroxyketone from epsilon-caprolactone, and an effective one-step deprotection strategy to remove all protecting groups using 0.2 N HCl.

摘要

已成功实现了新型、高效的 sphingofungin F 全合成，总收率为 10.4%，历经 15 步反应。该合成的显著特点包括：利用甲基三环亚胺内酯 3 进行不对称羟醛缩合反应作为关键步骤，以引入两个所需的手性中心；通过一步反应，从ε-己内酯合成ω-羟基酮；采用 0.2 N HCl 进行有效一步脱保护策略，去除所有保护基团。