Journal of the American Chemical Society

Total synthesis of (.+-.)-chondrillin,(.+-.)-plakorin, and related peroxy ketals. Development of a general route to 3, 6-dihydro-1, 2-dioxin-3-ols

BB Snider, Z Shi

Index: Snider, Barry B.; Shi, Zhongping Journal of the American Chemical Society, 1992 , vol. 114, # 5 p. 1790 - 1800

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Citation Number: 52

Abstract

Abstract: Seven-step syntheses of the antitumor cyclic peroxy ketals la, 2a, chondrillin (lb), and plakorin (2b) from (methoxymeth0xy) benzene (8) have been achieved in 26-28% overall yields. The key step is the photooxygenation of enone 4 with a sun lamp using rose bengal lactone or CuS04 as a sensitizer which gives a mixture of peroxy hemiketals 15 and 16 in 7545% yields. Acetal formation in acidic methanol completes the syntheses of 1 and ...