Synthesis of tricyclic N,O-acetals from alpha-functionalized rubanone. A masked 1,2,3-tricarbonyl system from quinidine

A series of protected 2-bromorubanones derived from quinidine has been prepared diastereoselectively and converted into tricyclic N,O-acetals containing a masked 1,2,3-tricarbonyl functionality, Good yields have been achieved using formyl-, acetyl-and propionyl-protecting groups. The novel one-pot c...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 4; pp. 801 - 806
Main Authors Langer, P, Frackenpohl, J, Hoffmann, HMR
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.02.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CINCHONA ALKALOIDS
COMBINED NMR
TETRAZOMINE
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Summary:A series of protected 2-bromorubanones derived from quinidine has been prepared diastereoselectively and converted into tricyclic N,O-acetals containing a masked 1,2,3-tricarbonyl functionality, Good yields have been achieved using formyl-, acetyl-and propionyl-protecting groups. The novel one-pot conversion of protected 2-bromorubanones into tricyclic Cinchona cage compounds is suggested to include a reduction-oxidation sequence and an intramolecular acyl transfer.
ISSN:1472-7781
0300-922X
1364-5463
DOI:10.1039/a705561g