☆ 4.4 Article

Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

TETRAHEDRON (2015)

Journal

TETRAHEDRON

Volume 71, Issue 38, Pages 6961-6978

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tet.2015.07.010

Keywords

Captodative alkenes; 1-Acetylvinyl p-nitrobenzoyloxy; alpha-Ketols; Actinopolymorphol B; Tanakine; 4-Oxazolin-2-ones

Categories

Chemistry, Organic

Funding

SIP-IPN [20110172, 20120830, 20130686, 20140858, 20150917]
CONACYT [83446, 178319]
PIFI-IPN program for scholarship
Ludwig K. Hellweg Foundation

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Abstract

Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

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