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Synfacts 2018; 14(06): 0553
DOI: 10.1055/s-0037-1609850
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Daphniphyllum Alkaloids

Contributor(s):
Erick M. Carreira
,
Robert J. Gillespie
Zhang W. Ding M. Li J. Guo Z. Lu M. Chen Y. Liu L. Shen Y.-H. Li A. * Shanghai Institute of Organic Chemistry and Second Military Medical University, Shanghai, P. R. of China
Total Synthesis of Hybridaphniphylline B.

J. Am. Chem. Soc. 2018;
140: 4227-4231
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Publication History

Publication Date:
17 May 2018 (online)

 
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Key words

(–)-hybridaphni-phylline B - daphniphyllum alkaloids - Diels–Alder cycloaddition - Claisen rearrangement - biomimetic synthesis

Significance

The first total synthesis of (–)-hybridaphniphylline B in addition to three other daphniphyllum alkaloids was accomplished. The synthetic strategy relied on a biomimetic Diels–­Alder cycloaddition to forge the stereochemically dense decacyclic skeleton.


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Comment

Utilizing previously synthesized A (J. Am. Chem. Soc. 2017, 139, 14893), hexacycle D was accessed in eleven steps through an optimized Claisen rearrangement. D served as a common intermediate for the synthesis of four natural products.


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