TOTAL SYNTHESIS OF D,L-PURPUROSAMINE C

Article abstract of DOI:10.1016/S0040-4020(01)89993-2

Methyl 2,6-diacetamido-2,3,4,6-tetradeoxy-α-D,L-erythropyranoside (methyl 2,6-N,N-diacetyl-D,L-purpurosamidine C) was synthesized from N-tert-butoxycarbonylaminoethanol and l-methoxybuta-1,3-diene in a seven-step reaction sequence. (4+2)Cycloaddition of diene 1 to N-protected α-amino aldehyde 2 and hydroboration of the adduct formed are key steps in the synthetic sequence.