Total synthesis of antillatoxin.
The total synthesis of natural (4R,5R)-antillatoxin and its analog (4S,5S)-antillatoxin has been achieved; the optically pure key intermediates were prepared from indium mediated allylation of either primary or secondary allylic bromide with aldehyde in aquoues media, followed by highly selective Luche's reduction and chiral resolution.
Lee
Kiew-Ching
KC
Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore 637616.
Loh
Teck-Peng
TP
D000447:Aldehydes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D007204:Indium / Q000737:chemistry; D055666:Lipopeptides; D009842:Oligopeptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D000498:Allyl Compounds; D055666:Lipopeptides; D009842:Oligopeptides; D010456:Peptides, Cyclic; C121886:antillatoxin; D007204:Indium; C050431:allyl bromide