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Org Lett. 2012 Jul 6;14(13):3264-7. doi: 10.1021/ol301154f. Epub 2012 Jun 21.

Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.

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1
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

Abstract

In this study we used sequential catalysis-PPh(3)--catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization--to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.

PMID:
22721256
PMCID:
PMC3391320
DOI:
10.1021/ol301154f
[Indexed for MEDLINE]
Free PMC Article

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