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Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: Application to the Total Synthesis of the Natural Product (−)-5-epi-Vibsanin E

Schwartz, Brett; Denton, Justin R; Lian, Yajing; Davies, Huw ML; Williams, Craig


The total synthesis of (-)-5-epi-vibsanin E (2) has been achieved in 18 steps. The synthesis combines the rhodium-catalyzed [4 + 3] cycloaddition between a vinylcarbenoid and a diene to rapidly generate the tricyclic core with an effective end game strategy to introduce the remaining side-chains. The [4 + 3] cycloaddition occurs by a cyclopropanation to form a divinylcyclopropane followed by a Cope rearrangement to form a cycloheptadiene. The quaternary stereogenic center generated in the...[Show more]

CollectionsANU Research Publications
Date published: 2009
Type: Journal article
Source: Journal of the American Chemical Society
DOI: 10.1021/ja9019484


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