| Literature DB >> 29276813 |
Satoshi Fujita1, Keisuke Nishikawa2, Takayuki Iwata2, Taishi Tomiyama1, Hiroshi Ikenaga1, Kenji Matsumoto2, Mitsuru Shindo2.
Abstract
The first asymmetric total synthesis of (-)-stemonamine is described. The key reactions included intramolecular acylation to construct the seven-membered ring and a tandem [2+2] cycloaddition-Dieckmann condensation reaction using an ynolate to form the fully substituted cyclopentenone moiety. Racemization and epimerization of the natural product were first experimentally demonstrated.Entities:
Keywords: Dieckmann condensation; alkaloids; asymmetric synthesis; pyrrolo[1,2-a]azepine core; total synthesis; ynolate
Year: 2018 PMID： 29276813 DOI： 10.1002/chem.201706057
Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236