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通过平台萜烯(+)-双环吉马烯仿生合成(+)-ledene、(+)-绿花白千层醇、(-)-沼生醇、(+)-匙叶桉油烯醇以及紫苏醛A、C和D。

Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene.

作者信息

Tran Duc N, Cramer Nicolai

机构信息

Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9700.

出版信息

Chemistry. 2014 Aug 18;20(34):10654-60. doi: 10.1002/chem.201403082. Epub 2014 May 27.

Abstract

(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D.

摘要

(+)-双环吉马烯是一种存在于多种香精油中的具张力双环普通倍半萜。本文报道了一种以七步反应进行的简短且产率良好的双环吉马烯合成方法。这种萜类化合物用作仿生合成多种香树烯倍半萜类化合物(如里杜烯、绿花白千层醇、苍白甾醇和匙叶桉油烯醇)的关键平台中间体。此外,双环吉马烯被证明是杂萜类化合物西格多萜A、C和D合成中的萜类成分。

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