Total synthesis of natural (-)- and ent-(+)-4-desacetoxy-6,7-dihydrovindorosine and natural and ent-minovine:: Oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction

被引：75

作者：

Yuan, ZQ

Ishikawa, H

Boger, DL

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 04期

关键词：

D O I：

10.1021/ol050017s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation.

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页码：741 / 744

页数：4

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