Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride
| Title | Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride |
| Publication Type | Journal Article |
| Year of Publication | 2014 |
| Authors | Bhosale, SM, Momin, AA, Kunjir, S, Rajamohanan, PR, Kusurkar, RS |
| Journal | Tetrahedron Letters |
| Volume | 55 |
| Issue | 1 |
| Pagination | 155-162 |
| Date Published | JAN |
| ISSN | 0040-4039 |
| Keywords | Azoxybenzene, Calothrixin B, reduction, Sodium cyanoborohydride, Sodium methoxide |
| Abstract | During the total synthesis of calothrixin B, various novel and unexpected results were noticed such as cleavage of C-N bond in imine using sodium cyanoborohydride, sodium methoxide as a hydride source for reduction, deformylation in the presence of bromine, and deacylation using ceric ammonium nitrate (CAN). A detailed mechanism has been proposed for the unexpected results and a few of them are generalized. Temperature dependent NMR studies have been carried out for confirmation of the structure of one of the intermediates in the synthetic sequence. (C) 2013 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2013.10.140 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.379 |
Divison category:
Central NMR Facility