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Synthesis of (–)-Canataxpropellane
Total Synthesis of the Complex Taxane Diterpene Canataxpropellane.
20 April 2020 (online)
Key words(–)-canataxpropellane - taxane diterpenoid - [2+2] cycloaddition - pinacol coupling - 1O2 cycloaddition
(–)-Canataxpropellane is a taxane diterpenoid that was isolated from Taxus canadensis. Gaich and co-workers report the total synthesis of this structurally complex natural product. Key to the synthesis is an intramolecular [2+2] cycloaddition that forms the fully substituted cyclobutane.
Cyclobutane E was assembled in two steps from A and B through Diels–Alder cycloaddition and intramolecular [2+2] cycloaddition. 1O2 cycloaddition of F followed by reductive O–O bond cleavage gave H. Oxidation of diol L and pinacol coupling completed the carbon skeleton.