Synlett 2016; 27(19): 2721-2725
DOI: 10.1055/s-0036-1588310
letter
© Georg Thieme Verlag Stuttgart · New York

Diversity-Oriented Synthesis of cis-3,4-Dihydroxylated Piperidine and Its Higher Saturated and Unsaturated Homologues from d-Ribose and Their Glycosidase-Inhibition Study[1]

Sama Ajay
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur Road, Lucknow-226031, U. P., India   Email: akshaw55@yahoo.com
,
Inderpreet Arora
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur Road, Lucknow-226031, U. P., India   Email: akshaw55@yahoo.com
,
Puli Saidhareddy
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur Road, Lucknow-226031, U. P., India   Email: akshaw55@yahoo.com
,
Arun K. Shaw*
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur Road, Lucknow-226031, U. P., India   Email: akshaw55@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 16 June 2016

Accepted after revision: 11 August 2016

Publication Date:
31 August 2016 (online)


Zoom Image

Abstract

The synthesis of six-, seven-, and eight-membered cis-dihydroxy azacycles has been accomplished from d-ribose using Vasella reductive amination as a key step and utilization of hydroboration–oxidation, Mitsunobu reaction, and ring-closing metathesis (RCM) reactions in a facile manner. These homologous dihydroxylated heterocyclic scaffolds were subjected to the glycosidase inhibition assays. However, only a moderate inhibitory activity for three out of five compounds was observed against α-glucosidases with a high degree of selectivity.

Supporting Information