Synthesis 2016; 48(08): 1191-1196
DOI: 10.1055/s-0035-1561365
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Total Synthesis of Unnatural (+)-Anisomycin

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
,
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
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Publikationsverlauf

Received: 14. Dezember 2015

Accepted after revision: 18. Januar 2016

Publikationsdatum:
10. Februar 2016 (online)


Abstract

Stereoselective total synthesis of unnatural (+)-anisomycin from d-glucose has been achieved with an overall yield of 23%. The key synthetic features are regioselective opening of an epoxide, azidation of the resulting alcohol, and finally one-pot hydrogenation leading to cyclization to the pyrrolidine ring in a single step.

Supporting Information