Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization To Form Functionalized Hexahydropyrido[3,4-b]Indole

被引：5
作者：
Chen, Yi [1 ,2 ]
Song, Xuanyi [1 ,2 ]
Gao, Lu [1 ,2 ]
Song, Zhenlei [1 ,2 ]
机构：
[1] Sichuan Univ, Sichuan Engn Lab Plant Sourced Drug, West China Sch Pharm, Educ Minist & Sichuan Prov,Key Lab Drug Targeting, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Sichuan Res Ctr Drug Precis Ind Technol, Chengdu 610041, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 01期
关键词：
ENANTIOSELECTIVE TOTAL SYNTHESES; STEREOSELECTIVE MIGRATION; PETERSON OLEFINATIONS; AKUAMMILINE ALKALOIDS; EFFICIENT SYNTHESIS; N-ALLOC; VERSATILE; (+/-)-STRICTAMINE; DEAROMATIZATION; REARRANGEMENT;
D O I：
10.1021/acs.orglett.0c03806
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.
引用
收藏
页码：124 / 128
页数：5
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