Synthesis of 6-deoxy-homoDMDP and its C(5)-epimer: absolute stereochemistry of natural products from Hyacinthus orientalis

A concise enantioselective synthesis of 2,5-imino-2,5,6-trideoxy-d-manno-heptitol (6-deoxy-homoDMDP) and 2,5-imino-2,5,6-trideoxy-l-gulo-heptitol has been achieved. These compounds were used as stereochemical references to establish the absolute configuration of the corresponding naturally occurring stereoisomers, recently isolated from Hyacinthus orientalis. [Copyright &y& Elsevier]