Ferruginol

Ferruginol can be used for its antibacterial activities.

ChEBI: Ferruginol is an abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12. It has a role as an antineoplastic agent, an antibacterial agent, a protective agent and a plant metabolite. It is an abietane diterpenoid, a member of phenols, a carbotricyclic compound and a meroterpenoid.

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.

PARP | Bcl-2/Bax | Caspase | Antifection

[1] DAVID L. SNITMAN  David S W  Richard J Himmelsbach. Total synthesis of (.+-.)-ferruginol and (.+-.)-hinokione[J]. The Journal of Organic Chemistry, 1978, 43 25: 4758-4762. DOI:10.1021/jo00419a011.