In pursuit of pestalotiopsin a via zirconocene-mediated ring contraction.
[reaction: see text] An asymmetric route from the epimeric beta-hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).
Dong
Shuzhi
S
Evans Chemical Laboratories, The Ohio State University, Columbus, 43210, USA.
Parker
Gregory D
GD
Tei
Takahiro
T
Paquette
Leo A
LA
D002384:Catalysis; D003503:Cyclobutanes / Q000138:chemical synthesis*; D004952:Esters; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D003503:Cyclobutanes; D004952:Esters; D009942:Organometallic Compounds; D012717:Sesquiterpenes; C430595:pestalotiopsin A; C023398:Zirconocene dichloride; D015040:Zirconium