Aryne acyl-alkylation in the general and convergent synthesis of benzannulated macrolactone natural products: an enantioselective synthesis of (-)-curvularin.
A general approach for the synthesis of benzannulated macrolactone natural products utilizing an aryne acyl-alkylation reaction is described. Toward this end, the total syntheses of the natural products (-)-curvularin, curvulin, and (-)-diplodialide C are reported. Furthermore, the aryne insertion technology has enabled the rapid conversion of simple diplodialide natural products to curvularin, thereby connecting these two biosynthetically distinct classes of compounds via synthetic methods.
Tadross
Pamela M
PM
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Virgil
Scott C
SC
Stoltz
Brian M
BM
D000478:Alkylation; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D046911:Macromolecular Substances / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D015025:Zearalenone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001685:Biological Factors; D046911:Macromolecular Substances; D015025:Zearalenone; C013455:curvularin