Synfacts 2017; 13(06): 0565
DOI: 10.1055/s-0036-1590422
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Palhinine A and D

Erick M. Carreira
Marco Brandstätter
Wang F.-X. Du J.-Y. Wang H.-B. Zhang P.-L. Zhang G.-B. Yu K.-Y. Zhang X.-Z. An X.-T. Cao Y.-X. Fan C.-A. * Lanzhou University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), P. R. of China
Total Synthesis of Lycopodium Alkaloids Palhinine A and Palhinine D.

J. Am. Chem. Soc. 2017;
139: 4282-4285
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16. Mai 2017 (online)



Palhinine A and D are members of the Lycopodium alkaloid family isolated from the whole plant of Palhinhaea cernua L. Fan and co-workers describe the first total syntheses relying on a microwave-assisted regio- and stereoselective nitrone-alkene [3+2] cycloaddition as the key step to access the nine-membered azanone ring system.



Treatment of hydroxylamine E with formalin in CH2Cl2 resulted in the formation of nitrone F, which underwent an intramolecular 1,3-dipolar cycloaddition to give isoxazolidine G. N-Alkylation followed by reductive N–O cleavage gave access to the challenging azanone ring system, key structural motif of palhinine A and D.