Total synthesis of protected form of fungi metabolite cortalcerone

B Szechner, O Achmatowicz

Index: Szechner, Barbara; Achmatowicz, Osman Collection of Czechoslovak Chemical Communications, 1992 , vol. 57, # 1 p. 159 - 168

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Citation Number: 3

Abstract

Abstract Synthesis of methyl 4, 5-dideoxy-D, L-hex-4-enos-2-ulopyranosid-3-ulose ethylene acetal, derivative of the first natural sugar with dihydropyranone moiety, from 5- acetoxymethylfurfural is described. It was shown that 1, 3-transposition of the allylic alcohol in the dihydropyran ring, a key step of the synthesis, can be carried out via an intermediate allylic selenoxide with excellent regio-and stereoselectivity.