Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2+2] Cycloaddition Reaction

被引：42

作者：

Navarro, Raul ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

关键词：

CHLORINE-CONTAINING ALKALOIDS;

D O I：

10.1021/ol3017963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retroaldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating an unusual, caged, pentacyclic hemiketal product.

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页码：4354 / 4357

页数：4

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