A Concise and Unified Strategy for Synthesis of the C1–C18 Macrolactone Fragments of FD-891, FD-892 and Their Analogues: Formal Total Synthesis of FD-891
Organic Letters2014Vol. 16(19), pp. 5216–5219
Citations Over TimeTop 19% of 2014 papers
Naoki Kanoh, Ayano Kawamata, Tomohiro Itagaki, Y. Miyazaki, Kenzo Yahata, Eunsang Kwon, Yoshiharu Iwabuchi
Abstract
A concise and unified strategy for the synthesis of C1-C18 macrolactone fragments of FD-891 and FD-892 as well as their analogues is reported. The strategy includes a stereoselective vinylogous Mukaiyama aldol reaction (VMAR) using chiral silyl ketene N,O-acetal to construct C6-C7 stereocenters, an E-selective ring closing metathesis to construct a C12-C13 olefin, and stereodivergent construction of a C8-C9 epoxide.
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