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Synfacts 2017; 13(06): 0565
DOI: 10.1055/s-0036-1590422
DOI: 10.1055/s-0036-1590422
Synthesis of Natural Products and Potential Drugs
Synthesis of Palhinine A and D
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
Total Synthesis of Lycopodium Alkaloids Palhinine A and Palhinine D.
J. Am. Chem. Soc. 2017;
139: 4282-4285
Further Information
Publication History
Publication Date:
16 May 2017 (online)
Key words
palhinine A and D - Lycopodium alkaloids - nitrone - isooxazolidine - 1,3-dipolar cycloaddition
Significance
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.
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Comment
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.
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