Efficient strategy for the stereoselective synthesis of 2,3-disubstituted benzo[α]quinolizidine alkaloids: concise synthesis of (-)-protoemetinol

被引：10

作者：

Moon, Hyunyoung ^{[1
]}

An, Hongchan ^{[1
]}

Sim, Jaehoon ^{[1
]}

Kim, Kyeojin ^{[1
]}

Paek, Seung-Mann ^{[2
,3
]}

Suh, Young-Ger ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea

[2] Gyeongsang Natl Univ, Coll Pharm, Jinju 660751, South Korea

[3] Gyeongsang Natl Univ, Pharmaceut Sci Res Inst, Jinju 660751, South Korea

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

(-)-Protoemetinol; Benzo[alpha]quinolizidine alkaloid; Cross metathesis; Aza-Claisen rearrangement; Transannulation; ASYMMETRIC TOTAL-SYNTHESIS; CLAISEN REARRANGEMENT; PROTEIN-SYNTHESIS; IPECAC ALKALOIDS; IN-VITRO; EMETINE; ISOMERIZATION; TETRABENAZINE; (+/-)-EMETINE; TUBULOSINE;

D O I：

10.1016/j.tetlet.2014.12.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of (-)-protoemetinol has been accomplished through nine steps from a known homoallylic amine. The key steps of the synthesis involve the efficient preparation of an aza-Claisen rearrangement (ACR) precursor using cross metathesis and amide enolate-induced ACR followed by acid-catalyzed transannulation for the elaboration of the benzo[alpha]quinolizine skeleton and three stereogenic centers. This unique synthetic route envisages a unified and versatile strategy for the synthesis of 2,3-disubstituted benzo[alpha]quinolizidine. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：608 / 611

页数：4

共 77 条

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