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

Abstract

© Versita Sp. z o.o. Keywords: D 3 -trishomocubane • Aminoalcohol • Propeller chirality • Hydroxyketone Research ArticleThe rearrangement of easily accessible Cookson's diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.0 2,6 .0 3,10 .0 5,9 ]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.

Reactions of Cookson’s diketone with potassium halides in the polyphosphoric acid medium

“…The rearrangement of C S -trishomocubane (pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane) derivatives (1, Fig. 1) under acidic conditions is the most general approach for the synthesis of D 3 -trishomocubanes (2, Fig.…”