First stereoselective total synthesis of triumfettamide |
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Authors: | Thongam Joymati Devi Bishwajit SaikiaNabin C. Barua |
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Affiliation: | Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat 785006, Assam, India |
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Abstract: | The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units—α-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. |
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Keywords: | Triumfetta cordofolia Sphingolipid Phytoceramide Antimicrobial Stratum corneum |
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