American Chemical Society
ol201692h_si_001.pdf (4.05 MB)

Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C

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journal contribution
posted on 2011-08-19, 00:00 authored by Henning J. Jessen, Andreas Schumacher, Fabian Schmid, Andreas Pfaltz, Karl Gademann
Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation in high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner–Wadsworth–Emmons reaction. Deprotection gave synthetic (+)-torrubiellone C, which led to the assignment of the configuration of the natural product as (R).