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First enantioselective total synthesis of altersolanol A

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Abstract

The first enantioselective total synthesis of altersolanol A, a secondary metabolite from the endophytic fungi Stemphylium globuliferum and Alternaria solani, is described. The key step towards the tetrahydroanthraquinone core was an asymmetric DielsAlder (D–A) cycloaddition promoted by (R)-3,3′-diphenyl-BINOL/boron Lewis acid with good to excellent yields and excellent diastereo- and enantioselectivity (>95 : 5 dr and 98 : 2 er).

Graphical abstract: First enantioselective total synthesis of altersolanol A

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Publication details

The article was received on 28 Aug 2018, accepted on 28 Sep 2018 and first published on 01 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02113A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    First enantioselective total synthesis of altersolanol A

    B. Mechsner, B. Henßen and J. Pietruszka, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02113A

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