Application of the Dötz reaction to construction of a major portion of the ansa macrocycle (-)-kendomycin.
[Reaction: see text] A Dötz reaction employing a terminal alkyne and a Fischer-type alkenylchromium carbenoid led to a pentasubstituted benzene from which a major portion of the Streptomyces metabolite (-)-kendomycin was synthesized.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. james.white@oregonstate.edu
Smits
Helmars
H
D000480:Alkynes / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002857:Chromium / Q000737:chemistry; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D001555:Benzene Derivatives; D047029:Lactams, Macrocyclic; C485395:kendomycin; D002857:Chromium; D017828:Rifabutin; D001554:Benzene