Preparation and Conformational Study of B-Ring Substituted Lupane Derivatives

Author:

Dračínský Martin,Hybelbauerová Simona,Sejbal Jan,Buděšínský Miloš

Abstract

New lupane-type triterpenoids with 5(6) double bond were prepared using the method of partial demethylation on carbon C-4. Hydroboration of the double bond led to 6α-hydroxy derivative. By the oxidation and following reduction of 6α-hydroxy derivative the 6-oxo and 6β-hydroxy derivatives were prepared. A new method for selective oxidation of secondary hydroxy group in the presence of primary hydroxy group was performed. The conformation of ring A of new lupane-type 3-oxo derivatives with a substituent on ring B was elucidated on the bases of 1H and 13C NMR spectra and molecular modelling.

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

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