Synthesis 2017; 49(20): 4606-4612
DOI: 10.1055/s-0036-1589109
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Iminosugar Derivatives Based on a 2-Azabi­cyclo[4.1.0]heptane Skeleton

Alberto López-Rodríguez
Facultad de Farmacia, Dpto. Química y Bioquímica, Universidad San Pablo CEU, Urb. Montepríncipe, Boadilla del Monte, 28668 Madrid, Spain   eMail: jpercas@ceu.es
,
Gema Domínguez
Facultad de Farmacia, Dpto. Química y Bioquímica, Universidad San Pablo CEU, Urb. Montepríncipe, Boadilla del Monte, 28668 Madrid, Spain   eMail: jpercas@ceu.es
,
Facultad de Farmacia, Dpto. Química y Bioquímica, Universidad San Pablo CEU, Urb. Montepríncipe, Boadilla del Monte, 28668 Madrid, Spain   eMail: jpercas@ceu.es
› Institutsangaben
Funding of this project by Spanish MINECO and Fondo Europeo de Desarrollo Regional (FEDER, grant No. CTQ2015-64624-R MINECO/FEDER) and FUSP-CEU (PC17/16) is acknowledged.
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Publikationsverlauf

Received: 16. Juni 2017

Accepted after revision: 25. August 2017

Publikationsdatum:
12. September 2017 (online)


Abstract

Iminosugars are good starting points for the development of different kinds of drugs. Many are polyhydroxylated piperidines that behave as biomimetics of their corresponding pyranoses analogues. In the interaction with carbohydrate processing enzymes, selectivity is a crucial issue and the benefits of introducing a cyclopropane bridge in a piperidine structure is demonstrated. The synthesis of novel bicyclic piperidine-based iminosugars using a sulfur ylide cyclopropanation as the key synthetic step is described.

Supporting Information

 
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