Spiroketals via oxidative rearrangement of enol ethers.
Oxidative rearrangement of cyclic enol ethers leads to alpha-alkoxyesters. In the presence of a neighboring spiroether, this approach provides a stereoselective access to spiroketals. A modified proposal for the biosynthesis of acutumine is presented.
Waller
David L
DL
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, USA.
Stephenson
Corey R J
CR
Wipf
Peter
P
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry* / Q000378:metabolism; D004988:Ethers, Cyclic / Q000737:chemistry* / Q000378:metabolism; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D004988:Ethers, Cyclic; D007659:Ketones; D013141:Spiro Compounds; C442344:acutumine