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Synfacts 2025; 21(10): 977
DOI: 10.1055/a-2680-9046
Synthesis of Natural Products

Total Synthesis of (±)-Paxdaphnines A and B

Authors

Ren L, Lu Z, Wu D, Ma M, Li A *. Shanghai Institute of Organic Chemistry and University of Chinese Academy of Sciences, Shanghai, P. R. China
Total Synthesis of Paxdaphnine A and Daphlongamine B via Aza-Prins Cyclization Strategy.

J. Am. Chem. Soc. 2025;
147: 27137-27142
DOI: 10.1021/jacs.4c04779
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Keywords

(±)-paxdaphnine A - (±)-paxdaphnine B - Suzuki–Miyaura cross coupling - Kumada cross-coupling - Swern oxidation - nitrone dipolar cycloaddition - Pauson–Khand reaction - aza-Prins reaction

Significance

Li and co-workers report the first total synthesis of the daphniphyllum alkaloids (±)‑paxdaphnines A and B and (±)-daphlongamine B. (±)‑Paxdaphnine A possesses a highly congested heptacyclic scaffold with eight consecutive stereocenters. Pivotal for the successful construction of the molecule’s core were a nitrone dipolar cycloaddition and a Pauson–Khand reaction.


 

Comment

The synthesis commenced with coupling of enone A with alkene B. Effective decoration of the cycloheptane in D furnished oxime G in seven steps. Reduction of G and subsequent dioxolane deprotection generated directly a putative nitrone which, when heated in PhMe, gave isoxazole H. N–O bond reduction and elimination gave enyne I, which smoothly underwent Pauson–Khand reaction. (±)-Paxdaphnine B, accessed from enone J through functional group interconversions, was converted into (±)-paxdaphnine A by aza-Prins reaction.


 

 

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Artikel online veröffentlicht:
23. September 2025

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