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Published on: February 6, 2020
Formal total synthesis of (+)-neopeltolide
Sudhakar Athe1, Balla Chandrasekhar, Saumya Roy
1CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Abstract:
This paper describes the formal total synthesis of (+)-neopeltolide, a cytotoxic macrolide isolated from the marine sponge Neopeltidae. The key features of the synthesis include an asymmetric Evans alkylation to fix the C9-methyl center, Jacobsen hydrolytic kinetic resolution of terminal epoxides followed by their regioselective opening to fix the stereocenters at the C11 and C13 positions, respectively, a Pd-catalyzed oxa-Michael reaction to construct the tetrahydropyran ring, and Yamaguchi macrolactonization to form the macrocyclic core of the molecule.

