Synthesis of steroid intermediates via alkylation of dianion derived from acetoacetic ester

K. C. Wang, Chang Hsing Liang, Wai-Ming Kan, Shoei Sheng Lee

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A synthetic route for A-ring aromatic steroid intermediates starting from alkylation of dianion derived from acetoacetic ester with m-methoxyphenylethyl bromide to form benzene ring connected to a linear six-carbon fragment is described. This unit, after chemical modifications to 5, was condensed with 2-methylcyclopentan-1,3-dione (6a) to form prochiral trione, 7a, a key synthetic intermediate in A-ring aromatic steroid. Microbial reduction of 7a with Schizosaccharomyces pombe (NRRL Y-164) gave chiral (-)-11 in 65% yield. Starting from 2,2-dimethylsuccinic acid, 2,4,4-trimethylcyclopentan- 1,3-dione (6a) was prepared, which was condensed subsequently with 5 to form racemic 7b trione intermediate. Asymmetric cyclization of 7b in the presence of l-(-)-phenylalanine, followed by acidic cyclization led to regiospecific synthesis of 16,16-dimethyl tetracyclic steroid intermediate.

Original languageEnglish
Pages (from-to)27-34
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume2
Issue number1
DOIs
Publication statusPublished - 1994 Jan 1

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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