SYNTHETIC STUDIES ON INDOLE ALKALOIDS .7. EFFECT OF THE PIPERIDIEN RING SUBSTITUTION ON INTRAMOLECULAR KTBUO BF3ET2O CYCLIZATION OF THYL)-2-[1-(PHENYLSULFONYL)-3-INDOLYL]PIPERIDINES/

Authors
DIEZ A VILA C RUBIRALTA M
Citation
A. Diez et al., SYNTHETIC STUDIES ON INDOLE ALKALOIDS .7. EFFECT OF THE PIPERIDIEN RING SUBSTITUTION ON INTRAMOLECULAR KTBUO BF3ET2O CYCLIZATION OF THYL)-2-[1-(PHENYLSULFONYL)-3-INDOLYL]PIPERIDINES/, Tetrahedron, 49(19), 1993, pp. 4063-4072
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
19
Year of publication
1993
Pages
4063 - 4072
Database
ISI
SICI code
0040-4020(1993)49:19<4063:SSOIA.>2.0.ZU;2-C
Abstract
3,3-Disubstituted ethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-piperidine 4 shows a particular reactivity in front of KtBuO/BF3.Et2O: the interme diate spiroindolenine 15 evolves to a tryptophylpiperidinium salt, whi ch undergoes a Wagner-Meerwein rearrangement followed by a proton elim ination to yield the 2,3-disubstituted N-tryptophylpiperidine-3-acryla tes 19.