通过高效的 Helquist 稠环反应和双 N-烷基化反应全合成（-）-8-去氧血根碱。

Total synthesis of (-)-8-deoxyserratinine via an efficient Helquist annulation and double N-alkylation reaction.

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, China.

出版信息

Org Lett. 2010 Aug 6;12(15):3430-3. doi: 10.1021/ol1012444.

DOI:10.1021/ol1012444

PMID:20586438

Abstract

The first enantioselective total synthesis of (-)-8-deoxyserratinine has been achieved in 15 steps from enone 4 with 7% overall yield. The key features include a highly efficient Helquist annulation to furnish the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, as well as asymmetric Shi epoxidation, delivering the desired beta-epoxide stereospecifically.

摘要

首次从烯酮 4 经 15 步以 7%的总收率实现了 (-)-8-去氧血根碱的对映选择性全合成。关键特点包括高效的 Helquist 稠环反应构建顺式稠合的 6/5 双环、采用双 N-烷基化策略轻松构建氮杂九元环系统，以及不对称 Shi 环氧化，以立体特异性方式得到所需的 β-环氧化物。