Construction of the 1,2-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer

Molecules

Dawei Liang¹  Nana Gao¹  Wei Liu¹ 

[1] Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, China;

关键词: 1;    2-dialkenylcyclohexane;    (±)-geijerone;    Ireland-Claisen rearrangement;    intramolecular barbier reaction;    synthesis;   

DOI  :  10.3390/molecules19011238

来源: mdpi

【 摘 要 】

The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of (±)-geijerone and its diastereomer is reported. Construction of the syn- and anti-1,2-dialkenyl moiety was achieved via Ireland-Claisen rearrangement of the (E)-allylic ester, and the cyclohexanone moiety was derived from the iodoaldehyde via intramolecular Barbier reaction. The synthetic strategy allows rapid access to various epimers and analogues of elemene-type products.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.