Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene

Article abstract of DOI:10.1021/jo00125a042

The chiral bicyclic lactam 5, previously reported in the synthesis of (-)-α-cuparenone, was used to construct the more complex title compound 2.A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess.Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.