Abstract
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.
Original language | English |
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Pages (from-to) | 4758-4762 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 43 |
Issue number | 25 |
DOIs | |
State | Published - 1978 |
ASJC Scopus subject areas
- Organic Chemistry