A novel, efficient, diastereo- and enantioselective Mukaiyama aldol-based synthesis of a vinyl cyclopentanone core derivative of viridenomycin.
A strategy has been developed for a rapid seven-step construction of a chiral, nonracemic vinyl cyclopentanone building block as part of a synthetic approach to viridenomycin, using a diastereo- and enantioselective Mukaiyama aldol and intramolecular Knoevenagel condensation as key steps.
Batsanov
Andrei S
AS
Department of Chemistry, Durham University, Science Laboratories, South Road, Durham DH1 3LE, UK.
Knowles
Jonathan P
JP
Lightfoot
Andrew P
AP
Maw
Graham
G
Thirsk
Carl E
CE
Twiddle
Steven J R
SJ
Whiting
Andrew
A
D000447:Aldehydes / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis; D013237:Stereoisomerism
D000447:Aldehydes; D003517:Cyclopentanes; D007769:Lactams; C007201:cyclopentanone; C010374:viridinomycin; C116609:3-hydroxybutanal