Work

A stereoselective synthesis and nuclear magnetic resonance spectral study of four epimeric 17-hydroxy-16-ethylestranes.

Year: 1977

Type: article

Abstract: Four epimeric 17-hydroxy-16-ethylestr-4-en-3-ones (11) having potent antiandrogenic activity were prepared stereoselectively starting from 16α-ethyl-16β, 17β-diol monoacetate (2). The nuclear magnetic resonance spectra of the four epimers and other 16-substituted estranes and androstanes were investigated in order to elucidate the possibility for the assignment of the unknown configurations at the positions of 16 and 17. The data of the coupling constants (J16, 17) and the chemical shifts (13-methyl protons and 17-proton) can be used for the determination of the configuration at the positions of 16 and 17.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.25.1295

Authors: GIICHI GOTO, KOUICHI YOSHIOKA, KENTARO HIRAGA, TAKUICHI MIKI

Institution: Takeda (Japan)

Language: English

Topic: Steroid Chemistry and Biochemistry

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: bronze

OpenAlex ID: W1487205263

FWCI: 0.177

Cites:

Cited by: 22

Related to: 10