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. 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

Yi Chiao Fan  1 , Ohyun Kwon
Affiliations

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

Yi Chiao Fan et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
Rare fungal metabolites
Scheme 1
Scheme 1
Stepwise Formation of an Alkylidene Phthalan
Scheme 2
Scheme 2
Preliminary Investigation of Sequential-Catalysis
Scheme 3
Scheme 3
Proposed Reaction Mechanism
Scheme 4
Scheme 4
Syntheses of the Natural Products 3-Deoxyisoochracinic Acid, Isoochracinic Acid, and Isoochracinol
See this image and copyright information in PMC

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