Stereoselective Total Synthesis of Nemorosone

Stereoselective Total Synthesis of Nemorosone

The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]­nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described....

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Veröffentlicht in:Journal of organic chemistry 2012-06, Vol.77 (11), p.5098-5107
Hauptverfasser: Uwamori, Masahiro, Saito, Aya, Nakada, Masahisa
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung:The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]­nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300646j