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Issue 18, 2016
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‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent

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Abstract

Highly stereoselective total syntheses of sphingoid bases, natural bioactive ceramide sphinganine 1 (with an overall yield of 33%) and unnatural antineoplastic and antipsoriatic drug safingol 17 (with an overall yield of 38%) starting from chirons 3,4,6-tri-O-benzyl-D-galactal and 3,4,6-tri-O-benzyl-D-glucal respectively have been demonstrated. Mitsunobu reaction and late stage olefin cross metathesis are utilized as important steps in order to complete the total synthesis of these sphingoid molecules.

Graphical abstract: ‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent

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Article information


Submitted
21 Dec 2015
Accepted
25 Jan 2016
First published
27 Jan 2016

RSC Adv., 2016,6, 14505-14511
Article type
Paper
Author version available

‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent

P. Das, S. Kundooru and A. K. Shaw, RSC Adv., 2016, 6, 14505
DOI: 10.1039/C5RA27342K

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