Formation of gamma-lactones through CAN-mediated oxidative cleavage of hemiketals.
The generation of substituted gamma-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an alpha-heteroatom. Formation of the gamma-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.
Jacobine
Alexander M
AM
Department of Chemistry, University of New Hampshire, Durham, New Hampshire 30824, USA.
Lin
Weimin
W
Walls
Bethany
B
Zercher
Charles K
CK
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002563:Cerium / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D007659:Ketones; D007783:Lactones; C494217:phaseolinic acid; D002563:Cerium; D015107:4-Butyrolactone; C004653:ceric ammonium nitrate