Desymmetrizing Hydroformylation of Dihydromuconic Acid Diesters: Application to the Synthesis of (±)-Vindeburnol.

J Org Chem

Laboratoire d'Innovation Thérapeutique, UMR7200 CNRS/Université de Strasbourg, Faculté de Pharmacie , 74 route du Rhin, 67412 Illkirch, France.

Published: February 2017

The desymmetrizing hydroformylation of internal alkenes derived from dihydromuconic acid is described. The study of this reaction afforded easy access to polyfunction aldehydes. After the evaluation of the reactivity of the dimethyl ester derivative with various primary amines, this methodology was used to design a rapid synthesis of (±)-vindeburnol from tryptamine in only two steps.

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http://dx.doi.org/10.1021/acs.joc.6b02939DOI Listing

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