A concise and modular synthesis of pyranicin.
A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.
Department of Chemistry and Biochemistry, University of Colorado at Boulder, Boulder, Colorado 80309-0215, USA.
Nolan D
ND
Griggs
Andrew J
AJ
Phillips
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D005663:Furans; D007783:Lactones; C475590:pyranicin; C004511:butenolide; D015107:4-Butyrolactone