Synthetic Studies of Sesquiterpenes with the Dunniane Skeleton

被引：14
作者：
Pares, Sonia [1 ]
Alibes, Ramon [1 ]
Figueredo, Marta [1 ]
Font, Josep [1 ]
Parella, Teodor [2 ]
机构：
[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain
[2] Univ Autonoma Barcelona, Serv Ressonancia Magnet Nucl, E-08193 Barcelona, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 07期
关键词：
Photochemistry; Cycloaddition; Natural products; Small ring -systems; DIASTEREOSELECTIVE SYNTHESIS; HIGHLY EFFICIENT; VINYL SULFONES; CYCLOADDITION; DERIVATIVES; CONVERSION; METHYL; PHOTOCYCLOADDITION; CHEMISTRY; CARBON;
D O I：
10.1002/ejoc.201101614
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first synthetic approach to the entire carbon skeleton of the sesquiterpenes dunniane and cumacrene has been developed. The sequence features a [2+2] photochemical reaction of a chiral 2(5H)-furanone with ethylene to form the cyclobutane, a MeyerSchuster-type rearrangement of an a-acetylenic alcohol to an a,beta-unsaturated aldehyde, and a microwave-assisted DielsAlder reaction of an elaborated dienamine with methyl acrylate to construct the six-membered ring with the desired 1,4-substitution pattern.
引用
收藏
页码：1404 / 1417
页数：14
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