Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: Application to the Total Synthesis of the Natural Product (−)-5-epi-Vibsanin E
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Schwartz, Brett; Denton, Justin R; Lian, Yajing; Davies, Huw ML; Williams, Craig
Description
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]
Collections | ANU Research Publications |
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Date published: | 2009 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/59595 |
Source: | Journal of the American Chemical Society |
DOI: | 10.1021/ja9019484 |
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