Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D 3-trishomocubane)

Anastasiia Mishura 1 , Anna Sklyarova 1 , Dmitriy Sharapa 1 , Igor’ Levandovsky 1 , Michael Serafin 2 , Andrey Fokin 1 ,  and Vladimir Rodionov 1
  • 1 Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine
  • 2 Institute of Organic Chemistry, Justus-Liebig University, D-35392, Giessen, Germany

Abstract

The rearrangement of easily accessible Cookson’s diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.02,6.03,10.05,9]undecane-4-one, whose syn-stereochemistry was assigned through the X-ray crystal structure analysis. This key structure was used for the stereoselective synthesis of the D 3-trishomocubane derivatives as well as for the preparation of potential drugs bearing hydroxy- and amino-functional groups. A new multigram preparative synthesis of D 3-trishomocubane was developed.

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