Synthesis of carba sugars from aldonolactones. Part IV. Stereospecific synthesis of carbaheptopyranoses by radical-induced carbocyclisation of 2, 3-unsaturated …

SH Wagner, I Lundt

Index: Wagner, Sussi Holstein; Lundt, Inge Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 8 p. 780 - 788

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Citation Number: 11

Abstract

Three new carbaheptopyranoses, 6-deoxy-5a-carba-β-L-gulo-(8), 5a-carba-D-glycero-β-D- ido-(22) and 5a-carba-L-glycero-α-L-galacto-heptopyranose (25), have been prepared from 8-bromo-8-deoxy-2, 3-unsaturated octono-1, 4-lactones with L-galacto-, D-gluco-and D- manno-configuration, respectively. The key step was a regio-and stereoselective 6-exo-trig radical-induced carbocyclisation of the unsaturated octonolactones to give bicyclic ...

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