Concise asymmetric total synthesis of bruceolline J

Literature Information

Publication Date 2015-03-03
DOI 10.1039/C5QO00030K
Impact Factor 5.281
Authors

Dattatraya H. Dethe, Vijay Kumar B


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Abstract

We have developed a concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J, and a racemic approach employing an intramolecular rhodium carbenoid C–H insertion and highly regioselective gem-dimethylation reactions as key steps to synthesize bruceolline D, E along with (±)-bruceolline J.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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