An approach towards the total synthesis of (+)-epiquinamide and (+)-α-conhydrine from Garner aldehyde

被引：49

作者：

Srivastava, Ajay Kumar ^{[1
]}

Das, Sanjit Kumar ^{[1
]}

Panda, Gautam ^{[1
]}

机构：

[1] Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India

来源：

TETRAHEDRON | 2009年 / 65卷 / 27期

关键词：

N-BOC-2-ACYL OXAZOLIDINE METHODOLOGY; RING-CLOSING METATHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALPHA-CONHYDRINE; STEREOSELECTIVE SYNTHESIS; ENANTIOSPECIFIC SYNTHESIS; AZABICYCLIC ALCOHOLS; NATURAL-PRODUCTS; (-)-ALPHA-CONHYDRINE;

D O I：

10.1016/j.tet.2009.04.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and stereoselective route for the synthesis of 1-hydroxyquinolizidine, an advanced synthetic intermediate for the total synthesis of (+)-epiquinamide is presented. The key synthetic steps involve diastereoselective nucleophilic addition on L-serine derived Garner aldehyde and acid mediated (nSA) ring closing metathesis. The methodology is also elaborated successfully for the total synthesis of (+)-alpha-conhydrine, an important piperidine alkaloid. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5322 / 5327

页数：6

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