Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization | Zendy

Mariia S. Kirillova | Zendy; Michael E. Muratore | Zendy; Ruth Dorel | Zendy; Antonio M. Echavarren | Zendy

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Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

Author(s) -

Mariia S. Kirillova,

Michael E. Muratore,

Ruth Dorel,

Antonio M. Echavarren

Publication year - 2016

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.6b01428

Subject(s) - chemistry , ene reaction , cyclopropanation , enantiopure drug , isomerization , cycloaddition , alkyne , catalysis , claisen rearrangement , olefin fiber , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis

The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.

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