CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

13,14-Seco-steroids: A New Type of Modified Steroids Containing a Nine-Membered Ring

Authorized Users Only
1999
Authors
Bjelaković, Mira
Lorenc, Ljubinka
Pavlović, Vladimir D.
Mihailović, Mihailo Lj.
Tinant, Bernard
Declercq, Jean-Paul
Kalvoda, Jaroslav
Article (Published version)
Metadata
Show full item record
Abstract
Oxidations of 14α‐hydroxy‐5α‐cholestan‐3β‐yl acetate (5) with lead tetraacetate under thermal or photolytic conditions or in the presence of iodine proceed mainly by fragmentation of the C(13)−C(14) bond to give as the primary products the 13,18‐didehydro‐13,14‐seco derivative 6 and the (E )‐Δ12‐13,14‐seco ketone 11, respectively. Further transformations of these compounds under conditions of their formation afforded, in addition, the acetoxy derivatives 7 – 9 (from 6), and the D‐homo‐C‐nor compound 12 and (12R,13R)‐epoxide 13 (from 11). Unexpectedly, the photolytic lead‐tetraacetate oxidation of 5 resulted partly (to ca. 20%) in a reversible fragmentation involving scission and recombination of the C(8)−C(14) bond followed by formation of the 14β,22‐ether 10. Possible mechanisms for the observed transformations are discussed.
Keywords:
Steroids / Oxidation / Lead-tetraacetate / photolytic conditions / thermal conditions
Source:
Helvetica Chimica Acta, 1999, 82, 5, 707-721
Publisher:
  • Wiley

DOI: 10.1002/(SICI)1522-2675(19990505)82:5<707::AID-HLCA707>3.0.CO;2-O

ISSN: 0018-019X; 1522-2675

Scopus: 2-s2.0-0032920731
[ Google Scholar ]
14
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4184
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB