Facile synthesis of γ-alkylidenebutenolides from Morita–Baylis–Hillman adducts

An expedient synthetic procedure of γ-alkylidenebutenolides was developed via a sequential indium-mediated Barbier-type reaction of Morita–Baylis–Hillman bromide with aldehyde, lactonization, and double-bond isomerization. Various γ-alkylidenebutenolides including bovolide and its derivatives were s...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 53; no. 1; pp. 36 - 40
Main Authors:	Park, Bo Ram, Kim, Ko Hoon, Lim, Jin Woo, Kim, Jae Nyoung
Format:	Journal Article
Language:	English
Published:	Kidlington Elsevier Ltd 04-01-2012 Elsevier
Subjects:	Adducts Aldehydes Bromides Chemistry Derivatives Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Indium Isomerization Morita–Baylis–Hillman adducts Organic chemistry Preparations and properties Synthesis (chemistry) Tetrahedrons γ-Alkylidenebutenolides γ-Alkylidenebutenolides Morita–Baylis–Hillman adducts Indium Isomerization Lactone Organic bromine compounds Aldehyde Oxygen heterocycle Barbier reaction Morita-Baylis-Hillman adducts Lactonization Baylis-Hillman reaction Chemical synthesis Furan-2-one derivative Ethylenic compound
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Summary:	An expedient synthetic procedure of γ-alkylidenebutenolides was developed via a sequential indium-mediated Barbier-type reaction of Morita–Baylis–Hillman bromide with aldehyde, lactonization, and double-bond isomerization. Various γ-alkylidenebutenolides including bovolide and its derivatives were synthesized in good overall yields.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.11.001