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