刺桐烷和高刺桐烷生物碱的通用高效合成策略：（±）-3-去甲氧基刺桐定酮和（±）-刺桐曲胺的合成

General and efficient strategy for erythrinan and homoerythrinan alkaloids: syntheses of (+/-)-3-demethoxyerythratidinone and (+/-)-erysotramidine.

作者信息

Gao Shuanhu, Tu Yong Qiang, Hu Xiangdong, Wang Shaohua, Hua Rongbao, Jiang Yijun, Zhao Yuming, Fan Xiaohui, Zhang Shuyu

机构信息

State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, PRC.

出版信息

Org Lett. 2006 May 25;8(11):2373-6. doi: 10.1021/ol0607185.

DOI:10.1021/ol0607185

PMID:16706529

Abstract

[reaction: see text] A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides followed by a N-acyliminium ion promoted intramolecular cyclization, and represents one of the shortest routes to erythrinan and homoerythrinan alkaloids. As the application, the formal total synthesis of (+/-)-3-demethoxyerythratidinone and the total synthesis of (+/-)-erysotramidine have been achieved, respectively.

摘要

[反应：见正文] 已开发出一种用于合成芳香型和非芳香型刺桐烷类及高刺桐烷类生物碱的通用且高效的策略。该方法涉及一个关键的两步序列，即酮与各种N-取代碘乙酰胺的烷基化反应，随后是N-酰基亚胺离子促进的分子内环化反应，这是合成刺桐烷类和高刺桐烷类生物碱最短的路线之一。作为应用，分别实现了(±)-3-去甲氧基刺桐定酮的形式全合成和(±)-刺桐曲胺的全合成。