Photochemical and Thermal [2+2] Cycloaddition to Generate the Bicyclo[3.2.0]heptane Core of Bielschowskysin

被引：16

作者：

Farcet, Jean-Baptiste ^{[1
]}

Himmelbauer, Martin ^{[1
]}

Mulzer, Johann ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 20期

基金：

奥地利科学基金会;

关键词：

Total synthesis; Natural products; Terpenoids; Photochemistry; Oxidation; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ACID;

D O I：

10.1002/ejoc.201300382

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bicyclic core fragment of the marine diterpenoid bielschowskysin has been synthesized. First, a large library of precursors for a photochemical [2 + 2] cycloaddition was prepared and tested, but with limited success. In the end, a thermal [2 + 2] cycloaddition followed by appropriate regio- and stereocontrolled functionalization efficiently gave access to the desired bicyclo[3.2.0]heptane core. An optimized route to this remarkable molecular structure is presented.

引用

页码：4379 / 4398

页数：20

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