Studies on the synthesis of tedanolide: synthesis of the C(5)-C(21) segment via a highly stereoselective fragment assembly aldol reaction of a chiral beta,gamma-unsaturated methyl ketone.
[formula: see text] A highly diastereoselective synthesis of 3, corresponding to the C(5)-C(21) segment of tedanolide, has been accomplished by a route utilizing the aldol reaction of aldehyde 4 and the beta,gamma-unsaturated methyl ketone 5.
Roush
W R
WR
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu
Lane
G C
GC
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis; D018942:Macrolides; D008968:Molecular Conformation; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D007783:Lactones; D018942:Macrolides; D010446:Peptide Fragments; C116609:3-hydroxybutanal; C119775:tedanolide