Issue 22, 2014

Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: total synthesis of epiplakinic acid F

Abstract

The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration. The enantiomer of epiplakinic acid F methyl ester (2) was also prepared.

Graphical abstract: Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: total synthesis of epiplakinic acid F

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
27 Feb 2014
Accepted
02 Apr 2014
First published
02 Apr 2014

Org. Biomol. Chem., 2014,12, 3686-3700

Author version available

Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: total synthesis of epiplakinic acid F

X. Tian, J. Han, Q. Zhao and H. N. C. Wong, Org. Biomol. Chem., 2014, 12, 3686 DOI: 10.1039/C4OB00448E

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