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

Micah J. Niphakis; Gunda I. Georg

doi:10.1021/ol1023954

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

Micah J. Niphakis, Gunda I. Georg

Medicinal Chemistry

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68 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 language	English (US)
Pages (from-to)	196-199
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	2
DOIs	https://doi.org/10.1021/ol1023954
State	Published - Jan 21 2011

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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.",

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

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