crotogoudin and tetralin

crotogoudin has been researched along with tetralin* in 1 studies

Other Studies

1 other study(ies) available for crotogoudin and tetralin

Article	Year
Total Synthesis of Terpenoids Employing a "Benzannulation of Carvone" Strategy: Synthesis of (-)-Crotogoudin. Journal of the American Chemical Society, 2017, 08-23, Volume: 139, Issue:33 Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the α-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the ent-3,4-seco-atisane diterpenoid (-)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels-Alder cycloaddition with ethylene gas (to construct the bicyclo[2.2.2]octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of ent-3,4-seco-abietane diterpenoids using an intramolecular oxidative dearomatization. Topics: Biological Products; Cycloaddition Reaction; Cyclohexane Monoterpenes; Diterpenes; Ethylenes; Monoterpenes; Oxidation-Reduction; Stereoisomerism; Tetrahydronaphthalenes	2017

Article

Year

Total Synthesis of Terpenoids Employing a "Benzannulation of Carvone" Strategy: Synthesis of (-)-Crotogoudin.

Journal of the American Chemical Society, 2017, 08-23, Volume: 139, Issue:33

Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the α-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the ent-3,4-seco-atisane diterpenoid (-)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels-Alder cycloaddition with ethylene gas (to construct the bicyclo[2.2.2]octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of ent-3,4-seco-abietane diterpenoids using an intramolecular oxidative dearomatization.

Topics: Biological Products; Cycloaddition Reaction; Cyclohexane Monoterpenes; Diterpenes; Ethylenes; Monoterpenes; Oxidation-Reduction; Stereoisomerism; Tetrahydronaphthalenes

2017