Synfacts 2020; 16(10): 1133
DOI: 10.1055/s-0040-1705889
Synthesis of Natural Products and Potential Drugs

Synthesis of (±)-Cryptotrione

Contributor(s):
Erick M. Carreira
,
Hendrik Bulthaupt
Lyu M.-Y, Zhong Z, Lo VK.-Y, Wong HN. C, *, Peng X.-S. * The Chinese University of Hong Kong, P. R. of China
Total Synthesis of Cryptotrione.

Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.202009255.
 

Significance

Cryptotrione was isolated from the bark of Cryptomeria japonica in 2010. It has anticancer activity against human oral epidermoid carcinoma KB cells. Additionally, it consists of an unprecedented skeleton featuring an abietane-type diterpene quinone methide spiro-fused to a thujone-type bicyclo[3.1.0]hexane. Wong, Peng, and co-workers present the first total synthesis of (±)-cryptotrione.


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Comment

Literature-known ester A was converted into enyne B in eight steps. Subsequent platinum-catalyzed enyne cycloisomerization gave spiro-fused tetracycle C. Following functional group transformations, diene F underwent polyene cyclization to afford G. Further elaboration of this intermediate yielded (±)-cryptotrione in 13 additional steps.


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Publication History

Publication Date:
17 September 2020 (online)

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