Synthesis of the beta-hydroxydopa-gamma-hydroxy-delta-sulfinylnorvaline component of ustiloxins A and B.
The dopa-sulfinylnorvaline component of ustiloxins A and B has been prepared using an Evans salen-Al-catalysed aldol reaction with a 6-mercaptoisovanillin derivative, followed by incorporation of the norvaline group and asymmetric oxidation of the resulting sulfide to give the corresponding sulfoxide.
Hunter
Luke
L
School of Chemistry, University of Sydney, NSW, Australia.
McLeod
Malcolm D
MD
Hutton
Craig A
CA
D001547:Benzaldehydes / Q000737:chemistry; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009183:Mycotoxins / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry; D013454:Sulfoxides / Q000138:chemical synthesis / Q000737:chemistry; D014633:Valine / Q000031:analogs & derivatives / Q000737:chemistry
D001547:Benzaldehydes; D009183:Mycotoxins; D010456:Peptides, Cyclic; D013440:Sulfides; D013454:Sulfoxides; C089077:ustiloxin B; C087237:ustiloxin A; C093382:isovanillin; D004295:Dihydroxyphenylalanine; C005313:norvaline; D014633:Valine