Formal stereoselective synthesis of (+/-)-akagerine

Authors
Bennasar, ML Vidal, B Sufi, BA Bosch, J
Citation
Ml. Bennasar et al., Formal stereoselective synthesis of (+/-)-akagerine, CHEM COMMUN, (23), 1998, pp. 2639-2640
Citations number
12
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
23
Year of publication
1998
Pages
2639 - 2640
Database
ISI
SICI code
1359-7345(199812):23<2639:FSSO(>2.0.ZU;2-5
Abstract
A stereoselective synthesis of pentacyclic dilactam 1, a known precursor of the indole alkaloid akagerine, involving addition of the enolate of 1-acet ylindole 2 to 3-acetyl-2-fluoropyridinium salt 3, cyclization of the result ant IP-dihydropyridine, elaboration of the (E)-ethylidene substituent and c losure of the C ring by Pummerer reaction, is reported.