A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and …

…, H Maeda, M Hoshino, Y Iimura, T Suami

Index: Tadano, Kin-ichi; Maeda, Hiroo; Hoshino, Masahide; Iimura, Youichi; Suami, Tetsuo Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 1946 - 1956

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Citation Number: 61

Abstract

philic attack of the methylene of dimethyl malonate on both electrophilic termini (an aldehyde group and an iodomethylene group) of a L-arabinose derived intermediate. Although we achieved syntheses of pseudo-aD-glucopyranose13 and pseudo-@-L- altropyranose by using this one-step cyclization as a key reaction, lla competitive C- glycoside formation by C-0 bond formation in place of CC bond formation reduced the ...