Electrophilic cyclization of polyene allylsylanes. Synthesis of albicanyl acetate

Article abstract of DOI:10.1139/v82-098

The allylsilanes 5 (a, R=(CH3)2CCHCH2; b, R=(CH3)2CCHCH2CH2C(CH3)CHCH2) were prepared by a nickel(II) catalyzed coupling of trimethylsilylmethylmagnesium chloride with the enol phosphate of the corresponding β-keto esters.Stannic chloride and mercuric trifluoroacetate effected a cyclization of 5.The product from 5b was converted into the marine natural product, albicanyl acetate (1).