Biomimetic synthesis of phaitanthrin e involving a fragmentation of sp(3) carbon-carbon bond: synthesis and rearrangement of phaitanthrin D to phaitanthrin E
| Title | Biomimetic synthesis of phaitanthrin e involving a fragmentation of sp(3) carbon-carbon bond: synthesis and rearrangement of phaitanthrin D to phaitanthrin E |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Vaidya, SD, Argade, NP |
| Journal | Organic Letters |
| Volume | 17 |
| Issue | 24 |
| Pagination | 6218-6221 |
| Date Published | DEC |
| ISSN | 1523-7060 |
| Abstract | A biogenetic type total synthesis of alkaloids phaitanthrin D and phaitanthrin E has been described. The Csp(3)-Csp(3) bond cleavage with the release of several heteroatoms bearing unexpected leaving groups in intramolecular substitution reactions on an iminium double bond in the quinazolinones has been demonstrated using HMDS/ZnCl2 or NaHMDS. The mechanistic aspects have been supported by isolation and characterization of appropriate intermediates. |
| DOI | 10.1021/acs.orglett.5b03203 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.732 |
Divison category:
Organic Chemistry