Journal
TETRAHEDRON
Volume 71, Issue 38, Pages 6961-6978Publisher
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
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Funding
- SIP-IPN [20110172, 20120830, 20130686, 20140858, 20150917]
- CONACYT [83446, 178319]
- PIFI-IPN program for scholarship
- Ludwig K. Hellweg Foundation
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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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