Toward the synthesis of reidispongiolide a: stereocontrolled synthesis of the C17-C22 and C23-C35 degradation fragments.
[structure: see text] By relying on the asymmetric aldol reactions of chiral ketones, a highly stereocontrolled synthesis of each of the C(17)-C(22) and C(23)-C(35) degradation fragments of reidispongiolide A has been achieved. This permits a configurational assignment of the complete C(17)-C(36) region of this antimitotic macrolide, along with providing advanced intermediates for a projected total synthesis.
Paterson
Ian
I
Department of Chemistry, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, United Kingdom. ip100@cam.ac.uk
Ashton
Kate
K
Britton
Robert
R
Knust
Henner
H
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007659:Ketones / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry
D000970:Antineoplastic Agents; D007659:Ketones; D018942:Macrolides; C476919:reidispongiolide A