CuBr2-catalyzed diastereoselective allylation: total synthesis of decytospolides A and B and their C6-epimers. Issue 14 (23rd March 2020)

• Record Type: Journal Article
• Authors: Padhi, Birakishore; Reddy, G. Sudhakar; Mallampudi, N. Arjunreddy; Choudhury, Utkal Mani; Mohapatra, Debendra K.
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 14(2020)
• Page Start: 2685
• Page End: 2695
• Publication Date: 2020-03-23
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02689d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient, cost effective and protecting group tolerant CuBr2 -catalyzed synthesis of 2, 6- trans -disubstituted tetrahydropyran with excellent diastereoselectivity, demonstrated in the total synthesis of decytospolides A and B and their C6-epimers. 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.