Synthesis of new 16-spirosteroids

Lutz F. Tietze, J. Wölfling, G. Schneider, Mathias Noltemeyer

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Reaction of estrone methyl ether 1 with sodium hydride and 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane, respectively, gives the 16-spirosteroid derivatives 2-4, which were reduced to the 17β-alcohols 7-9. Acetylation afforded the acetates 10-12. In the reaction of 1 and 1,3-dibromopropane a bis-allyl compound 5 and an annulated dihydropyran 6 were also formed. Cleavage of the ether moiety in 2 and 3 was accomplished with diisobutylaluminum hydride to give 3,17β-diols 13 and 14, respectively. (Steroids 59:305-309, 1994).

Original languageEnglish
Pages (from-to)305-309
Number of pages5
JournalSteroids
Volume59
Issue number5
DOIs
Publication statusPublished - 1994

Fingerprint

Allyl Compounds
Methyl Ethers
Acetylation
Estrone
Ether
Acetates
Steroids
Alcohols
Derivatives
1,3-dibromopropane
sodium hydride
diisobutylaluminum
1,5-dibromopentane
1,4-dibromobutane

Keywords

  • 16-spirosteroids
  • alkylation
  • DIBAH
  • α,ω-dibromoalkanes

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Molecular Biology

Cite this

Synthesis of new 16-spirosteroids. / Tietze, Lutz F.; Wölfling, J.; Schneider, G.; Noltemeyer, Mathias.

In: Steroids, Vol. 59, No. 5, 1994, p. 305-309.

Research output: Contribution to journalArticle

Tietze, Lutz F. ; Wölfling, J. ; Schneider, G. ; Noltemeyer, Mathias. / Synthesis of new 16-spirosteroids. In: Steroids. 1994 ; Vol. 59, No. 5. pp. 305-309.
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