Home

About

Advanced Search

Browse by Discipline

Scientific Societies

E-print Alerts

Add E-prints

E-print Network
FAQHELPSITE MAPCONTACT US


  Advanced Search  

 
5-Exo-dig Radical Cyclization of Enediynes: The First Synthesis of
 

Summary: 5-Exo-dig Radical Cyclization of
Enediynes: The First Synthesis of
Tin-Substituted Benzofulvenes
Serguei V. Kovalenko, Scott Peabody, Mariappan Manoharan,
Ronald J. Clark, and Igor V. Alabugin*
Department of Chemistry and Biochemistry, Florida State UniVersity,
Tallahassee, Florida 32306-4390
alabugin@chemmail.chem.fsu.edu
Received May 13, 2004
ABSTRACT
Bu3Sn-mediated 5-exo-dig radical cyclization of diaryl enediynes provides a mild and efficient approach to tin-substituted fulvenes. Further
synthetic opportunities opened by this process and general factors responsible for the observed regio- and stereoselectivity are outlined.
The astounding biological activity of natural enediyne
antibiotics1 is based on the transformation of (Z)-3-ene-1,5-
diyne moiety into reactive p-benzyne diradicals (the Bergman
cyclization).2 It has been suggested that these diradical
species can also be used as radical initiators in polymerization
of enediynes3
and other substrates.4
However, a clear

  

Source: Alabugin, Igor - Department of Chemistry and Biochemistry, Florida State University

 

Collections: Chemistry; Biology and Medicine