Biomimetic synthesis of phaitanthrin e involving a fragmentation of sp(3) carbon-carbon bond: synthesis and rearrangement of phaitanthrin D to phaitanthrin E

TitleBiomimetic synthesis of phaitanthrin e involving a fragmentation of sp(3) carbon-carbon bond: synthesis and rearrangement of phaitanthrin D to phaitanthrin E
Publication TypeJournal Article
Year of Publication2015
AuthorsVaidya, SD, Argade, NP
JournalOrganic Letters
Volume17
Issue24
Pagination6218-6221
Date PublishedDEC
ISSN1523-7060
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.

DOI10.1021/acs.orglett.5b03203
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)6.732
Divison category: 
Organic Chemistry