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

…, M Yamamoto, S Kohmoto, K Yamada

Index: Iwasa, Seiji; Yamamoto, Makoto; Kohmoto, Shigeo; Yamada, Kazutoshi Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2849 - 2853

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Citation Number: 10

Abstract

The fmt tandem radical cyclization of linear homdylic xanthates was explored. Homoallylic xanthates prepared from cr, o-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 y- ...