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

Birakishore Padhi; G. Sudhakar Reddy; N. Arjunreddy Mallampudi; Utkal Mani Choudhury; Debendra K. Mohapatra

doi:10.1039/C9OB02689D

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

Birakishore Padhi,^a G. Sudhakar Reddy,^a N. Arjunreddy Mallampudi,^a Utkal Mani Choudhury^a and Debendra K. Mohapatra

*^a

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* Corresponding authors

^a Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
E-mail: mohapatra@iict.res.in
Fax: +91-40-27160512
Tel: +91-40-27193128

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.

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Article information

DOI: https://doi.org/10.1039/C9OB02689D
Article type: Paper
Submitted: 18 Dec 2019
Accepted: 08 Mar 2020
First published: 09 Mar 2020

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Org. Biomol. Chem., 2020,18, 2685-2695

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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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Organic & Biomolecular Chemistry