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Synfacts 2021; 17(07): 0721
DOI: 10.1055/s-0040-1706236
DOI: 10.1055/s-0040-1706236
Synthesis of Natural Products and Potential Drugs
Synthesis of (+)-Manginoid A and (–)-Manginoid C
Zong Y,
Xu Z.-J,
*,
Zhu R.-X,
Su A.-H,
Liu X.-Y,
Zhu M.-Z,
Han J.-J,
Zhang J-Z,
Xu Y.-L,
Lou H.-X.
*
Shandong University, Jinan, P. R. of China
Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C.
Angew. Chem. Int. Ed. 2021;
DOI: 10.1002/anie.202104182.
Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C.
Angew. Chem. Int. Ed. 2021;
DOI: 10.1002/anie.202104182.
Key words
(+)-manginoid A - (–)-manginoid C - Kornblum oxidation - semipinacol rearrangement - radical cyclization - Suzuki–Miyaura coupling
Significance
Xu, Lou, and co-workers report the synthesis of manginoid and guignardone meroterpenoids. The highly oxygenated natural products feature a 6-oxabicyclo[3.2.1]octane skeleton. Isolated from the fungus Guignardia mangiferae, they display diverse biological activities.
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Comment
Kornblum oxidation of iodide C afforded unexpected ketone E. Pd-catalyzed coupling gave rise to alcohol I. Ketone J underwent semipinacol rearrangement to afford pivotal ketone K. Radical cyclization gave rise to peroxide L, completing the carbon skeleton of the natural product.
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Publication History
Article published online:
17 June 2021
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