Synthesis of 10,11-didehydro- and 10,11-dihydro-Quincorine and of the Quincoridine analogs: functionalized and enantiopure 1-azabicyclo[2.2.2]-octanes with four stereogenic centers

The convenient synthesis of 10,11-didehydro-QCI ( 2) and of 10,11-didehydro-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 ® 1 and Quincoridine ® 3 into the corresponding alkynes 2 and 4 involves twofold dehydr...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 9; no. 20; pp. 3717 - 3722
Main Authors Schrake, Olaf, Braje, Wilfried, Hoffmann, H.M.R., Wartchow, R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.10.1998
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CINCHONA ALKALOIDS
MOLECULAR MECHANICS
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Summary:The convenient synthesis of 10,11-didehydro-QCI ( 2) and of 10,11-didehydro-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 ® 1 and Quincoridine ® 3 into the corresponding alkynes 2 and 4 involves twofold dehydrobromination, and an important application of the solid KOH/aliquat 336 system in the key step. The structure of didehydro-QCI ( 2) has been elucidated by X-ray crystal diffraction. The new alkynes 2 and 4 are more polar and more basic than QCI and QCD, respectively.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00364-4