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Issue 15, 2018
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Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: synthesis of chiral furanolignans

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Abstract

An enantiospecific [3 + 2] annulation of γ-butyrolactone fused cyclopropanes with aromatic aldehydes was realized under Lewis acid catalysis. This method provides facile access to a series of chiral furanolignan derivatives bearing multiple contiguous stereogenic centers in good-to-excellent yields, exclusive diastereoselectivities and excellent enantiopurities under mild reaction conditions. Elaboration work on the product of this reaction delivers stereoisomeric analogues of (+)-virgatusin and suggests a structural revision might be necessary for a previously reported isolated natural product.

Graphical abstract: Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: synthesis of chiral furanolignans

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Publication details

The article was received on 22 Feb 2018, accepted on 21 Mar 2018 and first published on 22 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00455B
Citation: Org. Biomol. Chem., 2018,16, 2688-2696
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    Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: synthesis of chiral furanolignans

    Y. Shen, P. Yang, G. Yang, W. Chen and Z. Chai, Org. Biomol. Chem., 2018, 16, 2688
    DOI: 10.1039/C8OB00455B

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