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Synfacts 2024; 20(03): 0223
DOI: 10.1055/s-0043-1773085
Synthesis of Natural Products

Total Synthesis of (–)-Cephalocyclidin A

Contributor(s):
Erick M. Carreira
,
Vincent A. P. Ruf
Zhuang Q.-B, Tian J.-R, Lu K, Zhang X.-M, *, Zhang F.-M, Tu Y.-Q, *, Fan R, Li Z.-H, Zhang Y.-D. Lanzhou University and Shanghai Jiao Tong University, P. R. of China
Catalytic Asymmetric Polycyclization of Tertiary Enamides with Silyl Enol Ethers: Total Synthesis of (–)-Cephalocyclidin A.

J. Am. Chem. Soc. 2023;
145: 26550-26556
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Key words

(–)-cephalocyclidin A - asymmetric cyclization cascade - Wilkinson decarbonylation - Fleming–Tamao oxidation - Giese addition

Significance

Zhang, Tu and co-workers report a concise total synthesis of (–)-cephalocyclidin A. Key to their approach is a Cu(II)-catalyzed enantioselective polycyclization cascade of tertiary enamides with terminal silyl enol ethers. The development and scope of this methodology is also reported in the highlighted paper.


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Comment

Enamide E undergoes an intramolecular cyclization cascade to give H via nucleophilic attack of the enamine onto the carbonyl and subsequent trapping of the generated iminium with the enol ether. A second salient feature is the Giese addition, from K to L, furnishing the last carbocycle in the caged natural product.


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Publication History

Article published online:
14 February 2024

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