First stereoselective total synthesis of triumfettamide

作者：Devi Thongam Joymati; Saikia Bishwajit; Barua Nabin C^*

来源：Tetrahedron, 2013, 69(45): 9457-9462.

DOI：10.1016/j.tet.2013.08.068

• Triumfetta cordofolia
• Sphingolipid
• Phytoceramide
• Antimicrobial
• Stratum corneum

The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units-alpha-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1.

• 出版日期2013-11-11