Total synthesis of cystothiazoles A and B.
[structure: see text] Convergent enantioselective syntheses of the antifungal agents cystothiazoles A and B are described. The routes feature an asymmetric crotylation using a propargylic dicobalt hexacarbonyl complex, which provided enhanced diastereoselectivity over the uncomplexed propargylic acetal. The bisthiazole fragment was united with the side chain through a Stille cross-coupling of a terminal (E)-vinylstannane with a 4-trifloyl-substituted thiazole.
Shao
Jian
J
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D000935:Antifungal Agents / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis*; D017971:Tin Compounds / Q000737:chemistry
D000935:Antifungal Agents; D007202:Indicators and Reagents; D013844:Thiazoles; D017971:Tin Compounds; C112182:cystothiazole A; C112183:cystothiazole B