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Desilylation of α-trimethylsilylmethylene-δ-lactones. A new route to α-methylene-δ-lactones

✍ Scribed by Mario D Bachi; Eric Bosch

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
232 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Summaryr Addition of phenylthiol to a-trimethylsilylmethylene-r-lactones affords a-phenylthio(trhnethylsilyl)methyl-s-lactones which, on treatment with tetrabutylammonium fluorlde and methyl acrylate give the corresponding a-methylene-a-lactones through a one-pot double deblocking process.

The a-methylene-r-butyrolactone ring system constitutes a structural feature common to many natural products which exhibit interesting biological activities.1

We recently described a new method for the preparation of a-alkylidene-r-lactones, which is baaed on the intramolecular addition of alkoxycarbonyl free-radicals to acetylenes as displayed in Scheme 1.2 A variety of a-alkylldene-a-lactones

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α-Methylene lactones. VII. A facile rout
α-Methylene lactones. VII. A facile route to an oxygenated α-methylene-γ-butyrolactone
✍ Paul A. Grieco; Kunio Hiroi 📂 Article 📅 1974 🏛 Elsevier Science 🌐 French ⚖ 190 KB

The presence of an a-methylene-y-butyrolactone is essential for cytotoxic activity3 among the sesquiterpene lactones. Recently it has been established 3c,4 that the presence of a lipophilic, conjugated ester side chain located homoallylic to the exocyclic double bond of an a-methylene-ybutyrolactone