First synthesis of enantiopure 1,6-difunctionalized dodecahydrobenz[f] indenes

Jamie B. Scaglione, Nigam P. Rath, Douglas F. Covey

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)1089-1092
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number3
DOIs
StatePublished - Feb 4 2005

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