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Synthesis 2022; 54(08): 1977-1982
DOI: 10.1055/s-0041-1737339
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Total Synthesis of (+)-Kingianin A by Enantioselective Cycloaddition of Strained Cyclobutenone

Jie Zhang
a   Department of Chemistry and Biology, Jilin Provincial Key Laboratory of Carbon Fiber Development and Application, Changchun University of Technology, Changchun 130012, P. R. of China
,
Peng Yan
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
,
Zhichao Wang
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
,
Jinbo Zhao∗
a   Department of Chemistry and Biology, Jilin Provincial Key Laboratory of Carbon Fiber Development and Application, Changchun University of Technology, Changchun 130012, P. R. of China
,
Qin Chen∗
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
,
Ping Lu  ∗
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
› InstitutsangabenWe 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 - kingianins

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737339.
  • Supporting Information


Publikationsverlauf

Eingereicht: 09. November 2021

Angenommen: 08. Dezember 2021

Artikel online veröffentlicht:
08. Februar 2022

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