Abstract
The total synthesis of (±)-dysidiolide was accomplished with a high level of intramolecular stereo-induction. Methylation of 6-carboethoxy-3-chloro-5-methyl-cyclohex-2-enone provided 33 bearing the 6,7- trans-dimethyl substitution of the C6–C11 B-ring. Diastereoselective conjugate addition upon enone 34 installed the C11 stereogenic center. Annulation then provided an A-ring enone ( 23 ), a substrate for a challenging conjugate addition of the branched pentenyl side chain. The combination of tri- n-butylphosphine, boron trifluoride etherate, and a dialkylcuprate uniquely effected conjugate addition to yield 58 . Incorporation of the hydroxybutenolide-containing side chain completed the total synthesis and established the viability of a general approach for the preparation of the isolabdanoid terpene system.
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