Highly Stereoselective Synthesis of (+/-)-Aminobromocyclitol Derivatives from Furan

Reynard, E.; Reymond, J. L.; Vogel, P.

doi:10.1055/s-1991-20763

Highly Stereoselective Synthesis of (+/-)-Aminobromocyclitol Derivatives from Furan

1991

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Abstract

The Diels-Alder adduct (2-cyano-7-oxabicyclo[2.2.1]-hept-5-en-2-yl acetate) of furan and 1-cyanovinyl acetate was converted to N-[(1RS,2RS,3RS,4SR,6RS)-2,3,4-triacetoxy-6-bromocyclohex-1-yl]benzamide and to N-[(1RS,2RS,3SR,4RS,5SR,6SR)-2,3,4,5-tetraacetoxy-6-bromocyclohex-1-yl]b enzamide with high stereoselectivity.