Stereoselective tetrahydropyrido[2,1-a]isoindolone synthesis via carbanionic and radical intermediates: a model study for the Tacaman alkaloid D/E ring fusion

Authors
Hunter, R Richards, P
Citation
R. Hunter et P. Richards, Stereoselective tetrahydropyrido[2,1-a]isoindolone synthesis via carbanionic and radical intermediates: a model study for the Tacaman alkaloid D/E ring fusion, TETRAHEDR L, 41(19), 2000, pp. 3755-3758
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
19
Year of publication
2000
Pages
3755 - 3758
Database
ISI
SICI code
0040-4039(20000506)41:19<3755:STSVC>2.0.ZU;2-6
Abstract
Stereoselective cyclisation of melic acid-derived alpha-sulfanyllactam (1) via radical and carbanionic intermediates affords stereo-defined tetrahydro pyrido[2,1-a]isoindolones as model compounds for the D/E cis-ring fusion of the Tacaman indole alkaloid skeleton. A transition-state model to explain the stereoselectivity is presented. (C) 2000 Elsevier Science Ltd. All righ ts reserved.