Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.
A variety of chroman spiroketals are synthesized via inverse-demand [4 + 2] cycloaddition of enol ethers and ortho-quinone methides (o-QMs). Low temperature o-QM generation in situ allows for the kinetic, diastereoselective construction of these motifs, providing entry to a number of unusual chroman spiroketal natural products.
Marsini
Maurice A
MA
Department of Chemistry and Biochemistry, University of California at Santa Barbara Santa Barbara, California 93106-9510, USA.
Huang
Yaodong
Y
Lindsey
Christopher C
CC
Wu
Kun-Liang
KL
Pettus
Thomas R R
TR
D001688:Biological Products / Q000138:chemical synthesis*; D002839:Chromans / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001688:Biological Products; D002839:Chromans; D004987:Ethers; D005663:Furans; D045563:Indolequinones; D013141:Spiro Compounds; C520774:spiroketal; C068040:quinone methide