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Synfacts 2015; 11(6): 0569-0571
DOI: 10.1055/s-0034-1380782
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Schilancitrilactones B and C

Contributor(s):
Erick M. Carreira
,
Matthias Westphal
Wang L, Wang H, Li Y, Tang P * Nankai University, Tianjin, P. R. of China
Total Synthesis of Schilancitrilactones B and C.

Angew. Chem. Int. Ed. 2015;
54: 5732-5735
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Further Information

Publication History

Publication Date:
18 May 2015 (online)

 
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Key words

schilancitrilactone B - schilancitrilactone C - terpenoids - conjugate addition - radical coupling

Significance

Schilancitrilactones A, B, and C are terpenoid natural products recently isolated from Schisandra lancifolia, a plant used in traditional Chinese medicine. Schilancitrilactone C was shown to exhibit biological activity against HIV-1. The authors disclose total syntheses of schilancitrilactones B and C.


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Comment

Known compound A was converted into enone F in nine steps. Intramolecular conjugate addition in aqueous pyridine followed by ­epoxidation, E1cb-type ring opening, and conjugate reduction set the stage for iodination of the acetal in H. Radical coupling with stannane J afforded the two natural products.


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