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Synthesis 2022; 54(08): 1977-1982
DOI: 10.1055/s-0041-1737339
DOI: 10.1055/s-0041-1737339
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Total Synthesis of (+)-Kingianin A by Enantioselective Cycloaddition of Strained Cyclobutenone
We are grateful for the financial support from the National Natural Science Foundation of China (22071028, 21772024, 21921003).
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Abstract
We report here the first asymmetric total synthesis of (+)-kingianin A via dimerization of an enantioenriched bicyclo[4.2.0]octadiene. The synthesis features a chiral oxazaborolidinium ion catalyzed Diels–Alder reaction of strained cyclobutenone and stereoselective functionalization of the cyclobutane ring. A preliminary biological study indicated that (+)-kingianin A exhibits potent anticancer activities.
Key words
cyclobutenone - chiral oxazaborolidinium ion - Diels–Alder reaction - strain-release driven - bicyclo[4.2.0]octanes - kingianinsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737339.
- Supporting Information
Publication History
Received: 09 November 2021
Accepted: 08 December 2021
Article published online:
08 February 2022
© 2022. Thieme. All rights reserved
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