Intramolecular cyclopropanation of glycals: studies toward the synthesis of canadensolide, sporothriolide, and xylobovide.
[reaction: see text] The first examples of copper-catalyzed intramolecular cyclopropanations of glycal-derived diazoacetates are reported. The new cyclopropanes are converted into advanced intermediates for the synthesis of bislactone natural products. Synthetic highlights include the selective monodeprotection of a di-tert-butylsilylene ether and a zinc-mediated ring opening cascade reaction.
Yu
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M
Department of Chemistry and Biochemistry, The University of Texas at Austin, 78712, USA.
Lynch
V
V
Pagenkopf
B L
BL
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010165:Palladium; D011407:Propane / Q000737:chemistry
D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; C434312:canadensolide; C431475:xylobovide; C086157:sporothriolide; D010165:Palladium; D011407:Propane