Schneider F,
Samarin K,
Zanella S,
Gaich T.
* University of Konstanz, Germany
Total Synthesis of the Complex Taxane Diterpene Canataxpropellane.
Science 2020;
367: 676-681
Key words
(–)-canataxpropellane - taxane diterpenoid - [2+2] cycloaddition - pinacol coupling
-
1O
2 cycloaddition
Significance
(–)-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.
Comment
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.
