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Synfacts 2021; 17(11): 1175
DOI: 10.1055/s-0040-1720722
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (+)-Clionastatins A and B

Contributor(s):
Erick M. Carreira
,
Henry Lindner
Ju W, Wang X, Tian H, Gui J. * Shanghai Institute of Organic Chemistry, P. R. of China
Asymmetric Total Synthesis of Clionastatins A and B.

J. Am. Chem. Soc. 2021;
143: 13016-13021
DOI: 10.1021/jacs.1c07511
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Key words

(+)-clionastatin A - (+)-clionastatin B - androstanes - Ireland–Claisen rearrangement - Heck reaction - olefin dichlorination - structural revision

Significance

Gui and co-workers report the first total synthesis of (+)-clionastatins A and B, a novel class of polyhalogenated steroids isolated from a natural source. The synthesis led to revision of the originally proposed structures.


 

Comment

Acyl telluride C was accessed in three steps from enone A. Subsequent regioselective acyl radical addition afforded enol triflate E which underwent an intramolecular Heck reaction. Sultine I then allowed for diastereoselective dichlorination of the cyclohexene motive furnishing dichloride J. Finally, desaturation and chlorination gave rise to the natural products.


 

 

Publication History

Article published online:
19 October 2021

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