Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems

Izabella Jastrzebska, Jamie B. Scaglione, Gregory T. DeKoster, Nigam P. Rath, Douglas F. Covey

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

(Chemical Equation Presented) Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta-[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).

Original languageEnglish
Pages (from-to)4837-4843
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number13
DOIs
StatePublished - Jun 22 2007

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