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Issue 14, 2020
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CuBr2-catalyzed diastereoselective allylation: total synthesis of decytospolides A and B and their C6-epimers

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Abstract

An efficient CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides A and B and their C6-epimers.

Graphical abstract: CuBr2-catalyzed diastereoselective allylation: total synthesis of decytospolides A and B and their C6-epimers

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Supplementary files

Article information


Submitted
18 Dec 2019
Accepted
08 Mar 2020
First published
09 Mar 2020

Org. Biomol. Chem., 2020,18, 2685-2695
Article type
Paper

CuBr2-catalyzed diastereoselective allylation: total synthesis of decytospolides A and B and their C6-epimers

B. Padhi, G. S. Reddy, N. A. Mallampudi, U. M. Choudhury and D. K. Mohapatra, Org. Biomol. Chem., 2020, 18, 2685
DOI: 10.1039/C9OB02689D

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