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Stereoselective Synthesis of the Spirocyclic Ring System of the Sesquiterpene Spirolepechinene
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2019-03-21 , DOI: 10.1002/ajoc.201900151
Nina Duhamel 1 , Roberto Larcher 2 , Graziano Guella 3 , Lisa I. Pilkington 1 , Bruno Fedrizzi 1 , David Barker 1, 4
Affiliation  

Sesquiterpenes are a structurally diverse class of compounds that have been isolated from a wide range of living organisms. Spirolepechinene is a member of the rare spirojatamane class of sesquiterpenes with a unique relative stereochemistry about its spirocentre. While the other two members of this class have been synthesized, the differences in stereochemistry renders these previously‐reported methods not applicable to the synthesis of spirolepechinene. Herein we present an efficient method for the synthesis of the spirocyclic core of spirolepechinene that produces the required stereochemistry for this unique natural product with high diastereoselectivity.

中文翻译:

倍半萜烯螺烯的螺环系统的立体选择性合成

倍半萜是从多种活生物体中分离出来的一类结构多样的化合物。Spirolepechinene是倍半萜类的一种稀有螺茉莉烷烷类的成员,其螺中心具有独特的相对立体化学。虽然已经合成了该类别的其他两个成员,但立体化学的差异使这些先前报道的方法不适用于螺并戊烯的合成。本文中,我们提出了一种合成螺并戊二烯螺环核心的有效方法,该方法可为这种独特的天然产物产生所需的立体化学,并具有非对映选择性。
更新日期:2019-03-21
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