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Hypervalent Iodine(III)-Promoted Intermolecular C–C Coupling of Vindoline with β-Ketoesters and Related Substrates

Author:
Turner, Travis C., Shibayama, Kotaro, Boger, Dale L.
Source:
Organic letters 2013 v.15 no.5 pp. 1100-1103
ISSN:
1523-7052
Subject:
carbon-hydrogen bond activation, chemical bonding, chemical reactions, chemical structure, iodine, regioselectivity, vinblastine
Abstract:
The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, malononitriles, and β-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free hypervalent iodine(III)-promoted intermolecular sp³/sp² coupling, representing a special class of selective C–H activation with direct carbon–carbon bond formation, proceeds with generation of a quaternary center capable of incorporation of the vinblastine C16′ methyl ester and functionalized for subsequent divergent heterocycle introduction.
Agid:
5786546