A mild new procedure for production, cyclization and trapping of amidyl radicals: application to a formal total synthesis of peduncularine

Authors
Lin, XC Stien, D Weinreb, SM
Citation
Xc. Lin et al., A mild new procedure for production, cyclization and trapping of amidyl radicals: application to a formal total synthesis of peduncularine, TETRAHEDR L, 41(14), 2000, pp. 2333-2337
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
14
Year of publication
2000
Pages
2333 - 2337
Database
ISI
SICI code
0040-4039(20000401)41:14<2333:AMNPFP>2.0.ZU;2-Y
Abstract
Treatment of an olefinic hydroxamic acid with tert-butylsulfinyl chloride a nd Hunig's base from -50 degrees C to room temperature in the presence of a radical trap such as diphenyl diselenide, diphenyl disulfide or TEMPO affo rds a functionalized product derived from an amidyl radical cyclization. Th e methodology has been used in a formal total synthesis of the 6-azabicyclo [3.2.1] octane-containing indole alkaloid peduncularine. (C) 2000 Elsevier Science Ltd. All rights reserved.