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Synfacts 2021; 17(07): 0721
DOI: 10.1055/s-0040-1706236
Synthesis of Natural Products and Potential Drugs

Synthesis of (+)-Manginoid A and (–)-Manginoid C

Contributor(s):
Erick M. Carreira
,
Fabian Glatz
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;
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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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