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Synfacts 2023; 19(06): 0533
DOI: 10.1055/s-0042-1752539
Synthesis of Natural Products

Total Synthesis of (–)-Naphthospironone A

Contributor(s):
Erick M. Carreira
,
Sven M. Papidocha
Liu J.-X, Zhang S.-P, Sun F.-S, Li H, Gong Y.-L, *, Lu S.-C, *, Xu S. * Institute of Materia Medica, Beijing, P. R. of China
Asymmetric Total Synthesis of Naphthospironone A.

Angew. Chem. Int. Ed. 2023; e202303229
DOI: 10.1002/anie.202303229.
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Key words

(–)-naphthospironone - decarboxylative radical addition - Stille coupling - aldol addition - Mukaiyama hydration

Significance

Xu, Lu, Gong and co-workers present the first and asymmetric total synthesis of (–)-naphthospironone A. Isolated from an alkalophilic actinomycete in 2010, (–)-naphthospironone A exhibits moderate cytotoxic and antibiotic bioactivities.


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Comment

Early-stage Stille coupling of bromide C and stannane D assembled all carbon atoms of the natural product. Subsequent nucleophilic epoxidation and epoxide opening/lactonization provided spirocycle F. An intramolecular aldol cyclization of J completed the bridged carbocyclic skeleton. Mukaiyama hydration, sulfoxide formation/elimination and deprotection furnished (–)-naphthospironone A.


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Publication History

Article published online:
11 May 2023

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