Journal
ORGANIC LETTERS
Volume 24, Issue 7, Pages 1444-1447Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04383
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Funding
- Beijing Municipal Natural Science Foundation [19B10067]
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A six-step total synthesis of isohirsut-4-ene with a 5/5/5 tricyclic core has been achieved using a three-step strategy that involves a Rh(I)-catalyzed [5+2+1] cycloaddition, a Corey-Chaykovsky reaction, and a transannular epoxide-alkene cyclization. This strategy was further applied to synthesize more tricyclic analogues with one or two bridgehead quaternary centers.
A six-step total synthesis of isohirsut-4-ene with a 5/5/5 tricyclic core has been achieved. The synthesis features a Rh(I)-catalyzed [5+2+1] cycloaddition, a Corey-Chaykovsky reaction, and a transannular epoxide-alkene cyclization that afford the skeleton of the target molecule. This three-step strategy was further utilized to synthesize more 5/5/5 tricyclic analogues with one or two bridgehead quaternary centers.
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