Concise formal synthesis of (-)-(6R,11R,14R)-colletallol via D-proline catalysed alpha-aminooxylation-Wittig olefination strategy
| Title | Concise formal synthesis of (-)-(6R,11R,14R)-colletallol via D-proline catalysed alpha-aminooxylation-Wittig olefination strategy |
| Publication Type | Journal Article |
| Year of Publication | 2019 |
| Authors | Dey, S, Gadakh, S, Sudalai, A |
| Journal | Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry |
| Volume | 58 |
| Issue | 9 |
| Pagination | 1029-1036 |
| Date Published | SEP |
| Type of Article | Article |
| ISSN | 0376-4699 |
| Keywords | alpha-aminoxylation, Asymmetric synthesis, Enantioselectivity, Natural products, organocatalysis |
| Abstract | An efficient enantioselective formal synthesis of marine macrolide (-)-(6R,11R,14R)-colletallol has been achieved starting from commercially available raw materials. The key reactions include the D-proline catalyzed a-aminooxylation of aldehyde followed by Horner-Wardsworth-Emmons olefination in a sequential fashion to give the macrolide key intermediate 5 in high enantiomeric purity (97% ee) and high overall yield (32%). |
| Type of Journal (Indian or Foreign) | Indian |
| Impact Factor (IF) | 0.509 |
Divison category:
Chemical Engineering & Process Development
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