Total synthesis of ustiloxin D.
The total synthesis of ustiloxin D, a highly potent inhibitor of microtubule assembly, has been achieved. Notable features are the use of nucleophilic aromatic substitution (SNAr) for the construction of a chiral tertiary alkyl-aryl ether linkage, Sharpless asymmetric aminohydroxylation for the formation of the beta-hydroxytyrosine moiety, macrolactamization, and regioselective methylation.
Cao
Bin
B
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Park
Haengsoon
H
Joullié
Madeleine M
MM
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D010455:Peptides; D010456:Peptides, Cyclic; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000378:metabolism
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D009183:Mycotoxins; D010455:Peptides; D010456:Peptides, Cyclic; D014404:Tubulin; C089079:ustiloxin D