Original scientific paper

Steroidal Analogue of Deoxyvernolepin. Synthesis of d-Lactone Key Intermediate

Bogdan Šolaja ; Department of Chemistry, Faculty of Science, University of Belgrade, PO Box 550, YU -11001,Belgrade, Yugoslavia
Milutin Stefanović ; Department of Chemistry, Faculty of Science, University of Belgrade, PO Box 550, YU -11001,Belgrade, Yugoslavia

Abstract

Sesquiterpene lactones of elemanolide type vernolepin 1 and
deoxyvernolepin 2 exhibit a pronounced antitumor activity against
the Walker intramuscular carcinosarcoma 256 and CCRF - CEM
human lymphoblastic leukemia cells in culture and were therefore,
subjects of many partial and total syntheses. The synthesis of the steroidal analogue of deoxyvernolepin 3, i. e., its key interrnediate, d-lactone 28-hydroxy-2-oxa-5a,10a- cholest-6-en-3-one 4 starting from cholesterol is the subject of this report. Known reactions, as well as modified ones, were used in the synthesis. A new reaction for the preparation of dimethyl acetals with pyridinium chlorochromate and methanol was also developed. It was found that the acetalization reaction using pyridinium chlorochromate and methanol could be performed without affecting an acid-sensitive functional groups such as the oxirane ring.

Keywords

Hrčak ID:

177573

URI

https://hrcak.srce.hr/177573

Publication date:

16.5.1986.

Visits: 1.002 *