Enantioselective Construction of Cis-2,6-Disubstituted Dihydropyrans: Total Synthesis of (-)-Centrolobine

被引：41

作者：

Chaladaj, Wojciech ^{[1
]}

Kowalczyk, Rafal ^{[2
]}

Jurczak, Janusz ^{[1
,3
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Wroclaw Univ Technol, Dept Organ Chem, Fac Chem, PL-50370 Wroclaw, Poland

[3] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期

关键词：

DIELS-ALDER REACTION; STEREOSELECTIVE-SYNTHESIS; HIGH-PRESSURE; CLAISEN REARRANGEMENT; ASYMMETRIC-SYNTHESIS; PRINS CYCLIZATIONS; CONCISE SYNTHESIS; FORMAL SYNTHESIS; TETRAHYDROPYRAN; 1-METHOXYBUTA-1,3-DIENE;

D O I：

10.1021/jo902167r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper presents a simple and efficient route to chiral cis-6-substituted 2-(2-hydroxyethyl)-5,6-dihydro-2H-pyrans, a versatile chiral building block. The strategy is based on three key transformations: enantioselective hetero-Diels-Alder (HDA) reaction of aldehyde with Danishekky's diene, selective reduction of carbonyl function, and Claisen or related rearrangement. The synthetic utility of the methodology is illustrated by toal synthesis of antibiotic (-)-centolobine.

引用

页码：1740 / 1743

页数：4

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