Fully synthetic stereoselective routes to the differentially protected subunits of the tunicamycins

SJ Danishefsky, SL DeNinno, SH Chen…

Index: Danishefsky; DeNinno; Chen; Boisvert; Barbachyn Journal of the American Chemical Society, 1989 , vol. 111, # 15 p. 5810 - 5818

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Citation Number: 70

Abstract

Abstract: Total syntheses of the two subunits corresponding to tunicamycins have been achieved. One of the key steps involves a cyclocondensation reaction of 7-carbon aldehydo nucleoside with activated diene 8 under catalysis with stannic chloride (see 7+ 8-9a, b). Stereospecific Fitzsimmons cycloadditions of dibenzyl azodicarboxylate to galactal 12 and glucal22 simplified construction of the amino pyranose systems.