IMDA-radical cyclization approach to (+)-himbacine

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Abstract

(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.

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Wong, L. S. M., & Sherburn, M. S. (2003). IMDA-radical cyclization approach to (+)-himbacine. Organic Letters, 5(20), 3603–3606. https://doi.org/10.1021/ol0353058

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