First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f]indenes |
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Authors: | Scaglione Jamie B Rath Nigam P Covey Douglas F |
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Affiliation: | Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, St. Louis, MI 63110, USA. |
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Abstract: | 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. |
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