Concise and highly stereoselective syntheses of d-fagomine and 2-epi-fagomine. Issue 12 (23rd March 2016)

• Record Type: Journal Article
• Authors: Kallam, Srinivasa Reddy; Datrika, Rajender; Khobare, Sandip R.; Gajare, Vikas S.; Rajana, Nagaraju; Mohan, H. Rama; Babu, J. Moses; Siddaiah, V.; Pratap, T.V.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 12(2016)
• Page Start: 1351
• Page End: 1353
• Publication Date: 2016-03-23
• Subjects: Polyhydroxylated piperidine -- d-Fagomine -- 2-epi-Fagomine -- Inversion -- Double inversion; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.02.046
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Highly stereoselective total syntheses of polyhydroxylated piperidinesd -fagomine and 2- epi -fagomine have been developed starting from 3, 4, 6-tri- O -benzyl-d -glucal which is a derivative ofd -Glucose. Key steps in the synthesis of these azasugars involved N -Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N -Boc deprotection.