SYNTHESIS OF A C-11 SPIROPIPERIDINO DERIVATIVE OF 8-CHLORO-6,11-DIHYDRO 5H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDINE

Authors
AFONSO A KELLY J PUAR MS MCCOMBIE S MCPHAIL AT
Citation
A. Afonso et al., SYNTHESIS OF A C-11 SPIROPIPERIDINO DERIVATIVE OF 8-CHLORO-6,11-DIHYDRO 5H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDINE, Tetrahedron letters, 39(42), 1998, pp. 7661-7664
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
42
Year of publication
1998
Pages
7661 - 7664
Database
ISI
SICI code
0040-4039(1998)39:42<7661:SOACSD>2.0.ZU;2-E
Abstract
A method using N-tosyl aziridine for the synthesis of a spiropiperidin e 2 (R=H) is described. Cleavage of the N-tosyl group of the intermedi ate 8 to form the spiropiperidinone 9 was found to proceed in high yie ld with cone, sulfuric acid. Acylated derivatives of 2 were required f or a structure-activity study aimed at defining the spatial requiremen ts of the N-acyl residue in the lead Farnesyl-Protein-Transferase inhi bitor 1. (C) 1998 Elsevier Science Ltd. All rights reserved.