'Chiron' approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent. Issue 18 (3rd February 2016)

• Record Type: Journal Article
• Authors: Das, Pintu; Kundooru, Somireddy; Shaw, Arun K.
• Is Part Of: RSC advances. Volume 6:Issue 18(2016)
• Page Start: 14505
• Page End: 14511
• Publication Date: 2016-02-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5ra27342k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Highly stereoselective total syntheses of sphinganine1 and antineoplastic and antipsoriatic drug safingol17 have been demonstrated. Abstract : Highly stereoselective total syntheses of sphingoid bases, natural bioactive ceramide sphinganine1 (with an overall yield of 33%) and unnatural antineoplastic and antipsoriatic drug safingol17 (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.