Collect. Czech. Chem. Commun. 2007, 72, 1545-1552
https://doi.org/10.1135/cccc20071545

Preparation of Androstanes Related to Aphidicolin

Cavit Uyanika,*, Kudret Yildirimb, Aslihan Malayc, James R. Hansond and Peter B. Hitchcockd

a Department of Chemistry, University of Kocaeli, Izmit, 41380, Kocaeli, Turkey
b Department of Chemistry, University of Sakarya, Adapazari, 54187, Sakarya, Turkey
c Department of Chemistry, Gebze Institute of Technology, Gebze, 41400, Kocaeli, Turkey
d Department of Chemistry, University of Sussex, Brighton, Sussex, BN1 9QJ, U.K.

Abstract

The preparation of 3α,4α,17β-trihydroxy-, 3α,4α,16α,17α- and 2α,3α,16α,17α-tetrahydroxy-5α-androstane derivatives (5, 11, 18) from testosterone as steroidal analogues of diterpenoid inhibitor of DNA polymerase α, aphidicolin, is described. The crystal structure of 5α-androstane-3α,4α,17β-triyl triacetate (6) is reported.

Keywords: Aphidicolin; Steroids; Androstanes; Diterpenoids; Catalytic hydroxylation; X-Ray crystallography; DNA polymerase inhibitors.

References: 11 live references.