Toward the combinatorial synthesis of polyketide libraries: asymmetric aldol reactions with alpha-chiral aldehydes on solid support.
[reaction: see text] The viability of performing stereocontrolled aldol additions with alpha-chiral aldehydes attached by a silyl linker to a hydroxymethylpolystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipulation on the solid support leads to elaborate stereopentad sequences, as occur in 6-deoxyerythronolide B and discodermolide.
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cus.cam.ac.uk
Ian
I
Paterson
Taoues
T
Temal-Laïb
D000080:Acetals / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes; D002219:Carbamates; D002626:Chemistry, Pharmaceutical / Q000379:methods; D020650:Combinatorial Chemistry Techniques; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis*; D011753:Pyrones; D013237:Stereoisomerism
D000080:Acetals; D000447:Aldehydes; D000473:Alkanes; D002219:Carbamates; D007659:Ketones; D007783:Lactones; D011108:Polymers; D011753:Pyrones; C034277:6-deoxyerythronolide B; D004917:Erythromycin; C116609:3-hydroxybutanal; C071229:discodermolide