Stereospecific syntheses of (±)-ferruginol and (±)-hinokione were achieved in which the tricyclic ring system was assembled in the order C → BC → ABC. The key features of the approach involve: (1) the utilization of a lactone bridge as part of an enone protecting group in ring A; (2) the installation of an isopropyl group by the regioselective addition of lithium dimethylcuprate to a cross-conjugated dienone; (3) the elimination of the lactone bridge with concomitant aromatization of ring C; and (4) the reductive methylation of the enone in ring A to install the C-4 geminal dimethyl group and to guarantee the trans fusion of the AB rings.
|Number of pages||5|
|Journal||Journal of Organic Chemistry|
|State||Published - 1978|
ASJC Scopus subject areas
- Organic Chemistry