Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cinthia, 4 I-80126 Napoli, Italy
Abstract:
De novo synthesis of noncompetitive glycosidase inhibitors l-gulo-DNJ and l-talo-DNJ has been achieved in 9-10 steps starting from Garner’s aldehyde. Key to the success of this procedure was the construction of the 2,3-unsaturated piperidine 14, which syn dihydroxylation under Kishi’s and Donohoe’s conditions led to the desired iminosugars.