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IMDA-Radical Cyclization Approach to (+)-Himbacine

2003; American Chemical Society; Volume: 5; Issue: 20 Linguagem: Inglês

10.1021/ol0353058

1523-7060

Leon S.‐M. Wong, Michael S. Sherburn,

Chemical synthesis and alkaloids

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.