An asymmetric total synthesis of (+)-pentalenene

被引：16

作者：

Kim, Yoon-Jung ^{[1
]}

Yoon, Yeokwon ^{[1
]}

Lee, Hee-Yoon ^{[1
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

来源：

TETRAHEDRON | 2013年 / 69卷 / 36期

基金：

新加坡国家研究基金会;

关键词：

Stereoselective; Total synthesis; Triquinane; Trimethylenemethane; Tandem cycloaddition; ANGULAR TRIQUINANES; (+/-)-DEOXYPENTALENIC ACID; TRIMETHYLENEMETHANE DIYLS; (+/-)-PENTALENIC ACID; RADICAL CYCLIZATION; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; IDEAL SYNTHESIS; PENTALENENE; CYCLOADDITION;

D O I：

10.1016/j.tet.2013.05.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective total synthesis of (+)-pentalenene was achieved through the tandem cycloaddition reaction of the allenyl diazo substrate prepared from (+)-citronellal. The initial intramolecular [2+3] cycloaddition reaction between the diazo functionality and the allenyl group produced the trimethylenemethane (TMM) intermediate after immediate loss of nitrogen molecule from the cycloaddition intermediate. Subsequent [2+3] cycloaddition of the TMM with olefin produced the angularly fused triquinane structure stereoselectively. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7810 / 7816

页数：7

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