An enantioselective total synthesis of (+)-aigialospirol.
A concise and enantioselective total synthesis of (+)-aigialospirol is described here, featuring the first complex natural product synthesis that employs a cyclic ketal-tethered ring-closing metathesis strategy and an unexpected stereoselective epimerization of a benzylic hydroxyl group. The 15-step synthetic sequence illustrates the proof-of-concept that such an approach can be competitive with the classical spiroketal formation in the natural product synthesis.
Figueroa
Ruth
R
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705-2222, USA.
Hsung
Richard P
RP
Guevarra
Christle C
CC
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D015025:Zearalenone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D001572:Benzofurans; C484839:aigialospirol; C120440:hypothemycin; D015025:Zearalenone