Synthesis of tylocrebrine and related phenanthroindolizidines by VOF 3-mediated oxidative aryl-alkene coupling

Micah J. Niphakis, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

Abstract

A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

Original languageEnglish (US)
Pages (from-to)196-199
Number of pages4
JournalOrganic Letters
Volume13
Issue number2
DOIs
StatePublished - Jan 21 2011

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