Total synthesis of basiliskamides A and B.
[structure: see text] The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).
Lipomi
Darren J
DJ
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts, 02215, USA.
Langille
Neil F
NF
Panek
James S
JS
D000577:Amides / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D001232:Aspergillus fumigatus / Q000187:drug effects; D001685:Biological Factors / Q000138:chemical synthesis*; D002176:Candida albicans / Q000187:drug effects; D002384:Catalysis; D015394:Molecular Structure; D061065:Polyketides; D013237:Stereoisomerism
D000577:Amides; D000935:Antifungal Agents; D001685:Biological Factors; D061065:Polyketides; C504776:basiliskamide A; C504777:basiliskamide B