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
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.
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.
