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-me
A new route to α-methylene lactones
✍ Scribed by K.J. Divakar; P.P. Sane; A.S. Rao
- Publisher
- Elsevier Science
- Year
- 1974
- Tongue
- French
- Weight
- 110 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
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
A general procedure for the synthesis of a-methylene lactones cis-or trans-fused to larger rings is described. The convenient approach originates with two co-unsaturated aldehydes of the same or different chain length.
Model syntheses of a-methylene-y-butyrolactones have been achieved via an alkylationlactonlsatlon reaction of anthracene adducts la and lb with epoxides followed by release of the -methylene lactones through a retro Duels-Alder reactjon Numerous reports concerning the synthesis of a-methylene lacton