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Synfacts 2020; 16(05): 0493
DOI: 10.1055/s-0040-1707615
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Canataxpropellane

Rezensent(en):
Erick M. Carreira
,
Michael Schneider
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
CrossrefPubMedGoogle Scholar
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Publikationsverlauf

Publikationsdatum:
20. April 2020 (online)

 
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Key words

(–)-canataxpropellane - taxane diterpenoid - [2+2] cycloaddition - pinacol coupling - 1O2 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.


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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.


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