Enantioselective synthesis of guggultetrol and D-ribo-phytosphingosine tetraacetate via L-proline catalyzed sequential alpha-aminooxylation/Horner-Wardsworth-Emmons olefination-Sharpless asymmetric dihydroxylation strategy
| Title | Enantioselective synthesis of guggultetrol and D-ribo-phytosphingosine tetraacetate via L-proline catalyzed sequential alpha-aminooxylation/Horner-Wardsworth-Emmons olefination-Sharpless asymmetric dihydroxylation strategy |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Venkataramasubramanian, V, B. Kumar, S, Sudalai, A |
| Journal | Tetrahedron-Asymmetry |
| Volume | 26 |
| Issue | 10-11 |
| Pagination | 571-576 |
| Date Published | MAY |
| ISSN | 0957-4166 |
| Abstract | An efficient enantioselective synthesis of two bioactive molecules, that is, guggultetrol and D-ribo-phytosphingosine, is described with high enantioselectivity (>98% ee) starting from commercially available 1-hexadecanol. The synthesis comprises organocatalyzed sequential alpha-aminooxylation of an aldehyde followed by Horner-Wardsworth-Emmons olefination and Sharp less asymmetric dihydroxylation as the key chiral inducing steps. For both syntheses, gamma-hydroxy-alpha,beta-unsaturated ester serves as the common intermediate obtained from proline catalysis. (C) 2015 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetasy.2015.04.004 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.108 |
Divison category:
Chemical Engineering & Process Development