First synthesis of(+/-)-10 beta-hydroxy-13 beta-methylcyclohexa [a]quinolizidine. A convenient route to the ABC-part of 8-azasteroids.

Authors
Celanire, S Salliot-Maire, I Ribereau, P Godard, A Queguiner, G
Citation
S. Celanire et al., First synthesis of(+/-)-10 beta-hydroxy-13 beta-methylcyclohexa [a]quinolizidine. A convenient route to the ABC-part of 8-azasteroids., TETRAHEDRON, 55(30), 1999, pp. 9269-9282
Citations number
59
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
30
Year of publication
1999
Pages
9269 - 9282
Database
ISI
SICI code
0040-4020(19990723)55:30<9269:FSOBB[>2.0.ZU;2-W
Abstract
The first synthesis of racemic 10 beta-hydroxy-13 beta-methylcyclohexa[a]qu inolizidine is reported. Original construction of AC-bicyclic system is ach ieved by lateral metallation of 2-ethylpyridine followed by a Robinson anne lation, with the creation of a quaternary picolinic carbon center. Function alization of the A-ring and construction of the B-ring by a stereocontrolle d reduction of the pyridinium salt and final hydrogenations afford the ABC- part of an 8-azasteroid. (C) 1999 Elsevier Science Ltd. All rights reserved .