Stereoselective Synthesis of Higher Sugars by Homologation of Carbohydrate-Derived Enals with Nonracemic. gamma.-(Silyloxy) Allylic Stannanes and Substrate- …

JA Marshall, S Beaudoin

Index: Marshall, James A.; Beaudoin, Serge Journal of Organic Chemistry, 1994 ,  vol. 59,  # 22  p. 6614 - 6619

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Citation Number: 34

Abstract

A strategy is described for the chain extension of carbohydrate derivatives utilizing sequential Horner-Emmons condensation and then reduction-oxidation to prepare the enal homologue VII, which is converted to the corresponding dienyl bis-OTBS derivative M upon condensation with a y-(silyloxy) allylic stannane VI and subsequent silylation. Dihydroxylation of dienes M with 0~ 0 4-NMO leads to syn, anti, syn, anti, syn hexol ...