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IMDA-Radical Cyclization Approach to (+)-Himbacine

Wong, Leon; Sherburn, Michael

Description

(Equation presented) A formal total synthesis of the selective muscarinic receptor antagonist himbacine is presented. Key C-C bond-forming steps include an intramolecular Diels-Alder reaction, Stille coupling reactions, and a 6-exo-trig acyl radical cyclization to a conjugated enyne. An unexpected secondary alcohol to chloride conversion is witnessed during attempted thionocarbonate formation.

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
URI: http://hdl.handle.net/1885/85845
Source: Organic Letters
DOI: 10.1021/ol0353058

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