3 years ago

A Four-Step Synthesis of (±)-γ-Lycorane via Pd0-Catalyzed Double C(sp2)–H/C(sp3)–H Arylation

A Four-Step Synthesis of (±)-γ-Lycorane
via Pd0-Catalyzed Double C(sp2)–H/C(sp3)–H Arylation
David Dailler, Olivier Baudoin, Ronan Rocaboy
An expedient synthesis of lycorine alkaloids is reported using a palladium(0)-catalyzed double C–X/C–H arylation as the key step. The selectivity of this reaction was controlled through the judicious choice of the two halogen atoms, and its generality was demonstrated through the construction of various substituted pyrrolophenanthridinones. A selective arene hydrogenation allowed for the completion of the synthesis of (±)-γ-lycorane in just four steps from commercially available precursors.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03909

DOI: 10.1021/acs.orglett.7b03909

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