Unusual biomimetic oxidations of indoles: synthesis of suaveoline and an alkaloid G analogue

Authors
Bailey, PD Morgan, KM Rosair, GM Thomas, RL
Citation
Pd. Bailey et al., Unusual biomimetic oxidations of indoles: synthesis of suaveoline and an alkaloid G analogue, TETRAHEDR L, 40(47), 1999, pp. 8255-8259
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
47
Year of publication
1999
Pages
8255 - 8259
Database
ISI
SICI code
0040-4039(19991119)40:47<8255:UBOOIS>2.0.ZU;2-X
Abstract
The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) a nd suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochl oride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a sy nthesis of suaveoline can be oxidatively cyclized to 16. (C) 1999 Elsevier Science Ltd. All rights reserved.