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. 2012 May 18;14(10):2516-9.
doi: 10.1021/ol300800r. Epub 2012 May 3.

Total synthesis of (±)-sorocenol B employing nanoparticle catalysis

Huan Cong  1 , John A Porco Jr
Affiliations

Total synthesis of (±)-sorocenol B employing nanoparticle catalysis

Huan Cong et al. Org Lett. .

Abstract

The total synthesis of (±)-sorocenol B has been accomplished featuring key steps including silver nanoparticle (AgNP)-catalyzed Diels-Alder cycloaddition and late-stage Pd(II)-catalyzed oxidative cyclization. The synthetic natural product exhibited low micromolar cytotoxic activity against a number of human cancer cell lines.

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Figures

Scheme 1
Scheme 1
Biosynthesis of Sorocenol B and Related Natural Products
Scheme 2
Scheme 2
Retrosynthetic Analysis for Sorocenol B
Scheme 3
Scheme 3
Syntheses of Chalcone 11 and Diene 12
Scheme 4
Scheme 4
AgNP-Catalyzed Diels-Alder Cycloaddition of 11 and 12
Scheme 5
Scheme 5
Pd(II)-Catalyzed Oxidative Cyclization
Scheme 6
Scheme 6
Key NOE’s Leading to Relative Stereochemistry Assignments of 8 and 22
Scheme 7
Scheme 7
Synthesis of (±)-Sorocenol B
See this image and copyright information in PMC

References

    1. Astruc D, editor. Nanoparticles and Catalysis. Wiley-VCH; Weinheim, Germany: 2007.
    2. Myers VS, Weir MG, Carino EV, Yancey DF, Pande S, Crooks RM. Chem. Sci. 2011;2:1632.
    3. Patil NT. ChemCatChem. 2011;3:1121.
    1. Cong H, Porco JA. ACS Catal. 2012;2:65. - PMC - PubMed

    1. Cong H, Becker CF, Elliott SJ, Grinstaff MW, Porco JA. J. Am. Chem. Soc. 2010;132:7514. For a recent application of the AgNP catalyst to natural product synthesis, see: Chee CF, Lee YK, Buckle MJC, Rahman NA. Tetrahedron Lett. 2011;52:1797.

    1. Hano Y, Yamanaka J, Nomura T, Momose Y. Heterocycles. 1995;41:1035.

    1. Based on a Scifinder search as of March 26, 2012.

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