First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f]indenes.
An enantiospecific route to the previously unreported 1,6-difunctionalized dodecahydrobenz[f]indene ring system is described. Optically pure Hajos-Parrish ketone is used as the building block for preparation of a 6-methyleneinden-5-ol. This allylic alcohol is then utilized in a Claisen rearrangement under Johnson's conditions to introduce a side chain that is further modified and cyclized to produce the benz[f]indene ring system.
Scaglione
Jamie B
JB
Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, St. Louis, MI 63110, USA.
Rath
Nigam P
NP
Covey
Douglas F
DF
D018682:GABA Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry; D013329:Structure-Activity Relationship
D018682:GABA Agents; D007192:Indenes; D013256:Steroids