Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

Autor:	Shigeo Kohmoto, Seiji Iwasa, Makoto Yamamoto, Kazutoshi Yamada
Rok vydání:	1991
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Organic Chemistry Thiolactone Regioselectivity Free-radical reaction Radical initiator Chemoselectivity Cyclopentane Radical cyclization Medicinal chemistry Lactone
Zdroj:	The Journal of Organic Chemistry. 56:2849-2853
ISSN:	1520-6904 0022-3263
Popis:	The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic santhates prepared from α,β-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford γ-lactones in a high yield
Databáze:	OpenAIRE
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