A new synthesis of 2-C-methyl-D-ribono-1, 4-lactone and the C-9/C-13 fragment of methynolide

…, MS Pino-González, JF García-Aranda

Index: Lopez-Herrera, F. J.; Sarabia-Garcia, F.; Pino-Gonzalez, M. S.; Garcia-Aranda, J. F. Journal of Carbohydrate Chemistry, 1994 , vol. 13, # 5 p. 767 - 776

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Citation Number: 18

Abstract

Abstract The synthesis of the glucosaccharino lactone, 2-C-methyl-D-ribono-1, 4-lactone 7 from 2, 3-O-isopropylidene-D-glyceraldehyde 1 is reported. Lactone 7 was transformed into (2R, 3R)-2, 3-dihydroxy-2-methylpentanoic acid 18 (the C-9/C-13 fragment of Methynolid) by two new procedures which improve on existing alternatives: conversion of the epoxide derivative 9 to the episulfide 14 and subsequent reduction; and reductive opening of the 5 ...