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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).
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
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