Unusual stereochemical outcome of radical cyclization: synthesis of (+)-biotin
| Title | Unusual stereochemical outcome of radical cyclization: synthesis of (+)-biotin |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Chavan, SP, Chittiboyina, AG, Ramakrishna, G, Tejwani, RB, Ravindranathan, T, Kamat, SK, Rai, B, Sivadasan, L, Balakrishnan, K, Ramalingam, S, Deshpande, VH |
| Journal | Tetrahedron |
| Volume | 61 |
| Issue | 39 |
| Pagination | 9273-9280 |
| Date Published | SEP |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | biotin, exocyclization, radical cyclization |
| Abstract | An enantioselective synthesis of (+)-biotin 1 starting from naturally available cysteine is described. The key steps are the unusual stereochemical outcome of radical cyclization of compound 10 to prepare 5,5-fused system 11, and the introduction of C4-sidechain at C-6 in 13 via a Grignard reaction. (c) 2005 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2005.07.070 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.645 |
Divison category:
Organic Chemistry