Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of beta-amido aldehydes and revised structure of synthetic homolongamide

Authors
Sosa, ACB Yakushijin, K Horne, DA
Citation
Acb. Sosa et al., Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of beta-amido aldehydes and revised structure of synthetic homolongamide, TETRAHEDR L, 41(22), 2000, pp. 4295-4299
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
22
Year of publication
2000
Pages
4295 - 4299
Database
ISI
SICI code
0040-4039(20000608)41:22<4295:CCO2FS>2.0.ZU;2-0
Abstract
Pyrrole N-C and C-C bond-forming cyclizations are described with 2-pyrrolec arboxamidoacetals 1-3 under standard acetal deprotection conditions (pTsOH/ H2O) and with methanesulfonic acid. Under the former, N-C cyclization provi ded fused bi- and tricyclic systems bearing five- or six-membered rings, wh ile the latter produced six- and seven-membered C-C cyclized products. Furt hermore, an alternative structure for homolongamide 10 is proposed and is b ased on the facile solvation of beta-amido aldehyde 7. (C) 2000 Elsevier Sc ience Ltd. All rights reserved.