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A direct synthesis of α,β-butenolides by reaction of lithium β-lithioacrylates with carbonyl compounds

✍ Scribed by Drury Caine; A.Stephen Frobese

Book ID: 104237445
Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 257 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85840-8

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✦ Synopsis

A large number of biologically important natural products contain an a,&butenolide ring. 1 Much of the recent methodology on the synthesis of a,&butenolides which have the double bond unsubstituted or bearing alkyl substituents has been based upon the thermal fragmentation of ci-seleninyl' and a-3 or B-sulfinyl-y-lactones. 4 Other methods have involved selective reductions of y-hydroxy-a,&acetylenic acids, la,5 intramolecular cyclizations of a-acetoxy methyl ketones,6 heating of E-4-brow-2-butenoic acids,7 electrolytic decarboxylations of y-substituted paraconic acids, 8 pyrolysis of pyraxolines of y-butyrolactones, 9a &alkylidenebutyrolactones.gb and isomeriaations of Recently, we reported a convenient synthesis of y-butyrolactones (butanolides) by addition of lithium B-lithiopropionate to carbonyl compounds followed by lactonization. 10 We have now

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