SYNTHESIS OF 10,11-DIDEHYDRO-QUINCORINE AND 10,11-DIHYDRO-QUINCORINE AND OF THE QUINCORIDINE ANALOGS - FUNCTIONALIZED AND ENANTIOPURE 1-AZABICYCLO[2.2.2]-OCTANES WITH 4 STEREOGENIC CENTERS

Authors
SCHRAKE O BRAJE W HOFFMANN HMR WARTCHOW R
Citation
O. Schrake et al., SYNTHESIS OF 10,11-DIDEHYDRO-QUINCORINE AND 10,11-DIHYDRO-QUINCORINE AND OF THE QUINCORIDINE ANALOGS - FUNCTIONALIZED AND ENANTIOPURE 1-AZABICYCLO[2.2.2]-OCTANES WITH 4 STEREOGENIC CENTERS, Tetrahedron : asymmetry, 9(20), 1998, pp. 3717-3722
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
20
Year of publication
1998
Pages
3717 - 3722
Database
ISI
SICI code
0957-4166(1998)9:20<3717:SO1A1A>2.0.ZU;2-G
Abstract
The convenient synthesis of 10,11-didehydro-QCI (2) and of 10,11-dideh ydro-QCD (4) as well as 10,11-dihydro-QCI (5) and 10,11-dihydro-QCD (6 ) is described. Conversion of the olefinic double bond of Quincorine(R ) 1 and Quincoridine(R) 3 into the corresponding alkynes 2 and 4 invol ves twofold dehydrobromination, and an important application of the so lid KOH/aliquat 336 system in the key step. The structure of didehydro -QCI (2) has been elucidated by X-ray crystal diffraction. The new alk ynes 2 and 4 are more polar and more basic than QCI and QCD, respectiv ely. (C) 1998 Elsevier Science Ltd. All rights reserved.