Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol

An unprecedented deconstructive reorganization strategy for the de novo synthesis of hydroxylated benzofurans from kojic acid‐ or maltol‐derived alkynes is reported. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six‐carbon component. Through this strategy, at least one free hydroxyl group was introduced into the benzene ring in a substitution‐pattern tunable fashion without protection–deprotection and redox adjustment. With this method, a large number of hydroxylated benzofuran derivatives with different substitution‐patterns have been prepared efficiently. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran‐containing natural products (11 examples).

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Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

Zhang

Cao

Jiang

et al. 2020

Angewandte Chemie

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Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

et al. 2020

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Rapid Access to Oxa‐Bridged Bicyclic Skeletons through Gold‐Catalyzed Tandem Rearrangement Reaction

Zhang

Liao

Chen

et al. 2019

Chemistry A European J

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Ag old (I)-catalyzed reactiono fe nyne-etherst o rapidly construct oxa-bridged compoundsv ia at andem 1,2-acyloxy migration/intramolecularo xonium formation/ 1,2-rearrangement process was reported. The reaction was shown to be robust with aw ide range of substitution patterns tolerated to provide the corresponding oxygen-containing bridged products in good to excellent yields.Developing general and efficient methods for the construction of structurally diverse and complex polycyclic skeletons is important for natural products synthesis and lead discovery. [1] Oxygen-bridged bicyclic skeletons are ubiquitous structures in aw ide range of synthetic andn atural products, [2] such as Balsamiferine J, [2h] Englerin B, [2e] WaltherioneC, [2f] Mollanol A, [2g] Coutistatin A [2k] (Scheme 1). Highlye fficient construction of these oxa-bridged skeletons is one of the most important themes in organic synthesis. Much effort hasbeen made to de-Scheme1.Representative natural products with oxa-bridged bicyclic skeletons.Scheme2.Proposed gold-catalyzed propargyle ster rearrangements and further transformations.

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Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol

Cited by 3 publications

References 91 publications

Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

Rapid Access to Oxa‐Bridged Bicyclic Skeletons through Gold‐Catalyzed Tandem Rearrangement Reaction

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