Stereochemical Studies of Unsaturated Acetyl Steroids

Malka Gorodetsky, Dan Amar, Yehuda Mazur

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


The configuration and rotameric conformation of a number of β,γ-unsaturated acetyl steroids were established using ultraviolet absorption and circular dichroism data. It was found that the 4β-acetyl-5-ene system (in 6) and the 6β-acetyl-4-ene system (in 1 and 3) can be regarded as inherently disymmetric chromophores. On the other hand, the analogous β,γ-unsaturated acetyl group in 6α-acetyl-4-ene derivatives (2 and 9), 4β-acetyl-4α-methylandrost-5-en-3-on-17β-ol acetate (5), and also in 2β-acetyl-2α-methylandrost-5-en-17β-ol acetate (8), does not possess this characteristic. This conclusion facilitates the assignment of the configuration and conformation to the acetyl group and rings A and B in these compounds. The stereochemistry of alkylation of Δ4-3-keto steroids was determined using as a basis the configuration at C-4 of 4β-acetyl-4α-methylandrost-5-en-17β-ol (6).

Original languageEnglish
Pages (from-to)5218-5224
Number of pages7
JournalJournal of the American Chemical Society
Issue number23
StatePublished - 1 Dec 1964
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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