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This book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. The book first describes the total and formal synthesis of dictyodendrins A–F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds.
Organic chemistry. --- Catalysis. --- Inorganic chemistry. --- Chemistry. --- Medicinal chemistry. --- Pharmaceutical technology. --- Organic Chemistry. --- Inorganic Chemistry. --- Chemistry/Food Science, general. --- Medicinal Chemistry. --- Pharmaceutical Sciences/Technology. --- Physical sciences --- Pharmaceutical laboratory techniques --- Pharmaceutical laboratory technology --- Technology, Pharmaceutical --- Technology --- Chemistry, Medical and pharmaceutical --- Chemistry, Pharmaceutical --- Drug chemistry --- Drugs --- Medical chemistry --- Medicinal chemistry --- Pharmacochemistry --- Chemistry --- Inorganic chemistry --- Inorganic compounds --- Activation (Chemistry) --- Chemistry, Physical and theoretical --- Surface chemistry --- Organic chemistry --- Indole --- Chemistry, Inorganic. --- Synthesis.
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This book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. The book first describes the total and formal synthesis of dictyodendrins A–F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds.
Chemical thermodynamics --- Inorganic chemistry --- Organic chemistry --- Chemistry --- Enzymology --- Pharmacology. Therapy --- Clinical chemistry --- katalyse --- medische chemie --- organische chemie --- farmacologie --- chemie --- anorganische chemie
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Chemical thermodynamics --- Inorganic chemistry --- Organic chemistry --- Chemistry --- Enzymology --- Pharmacology. Therapy --- Clinical chemistry --- katalyse --- medische chemie --- organische chemie --- farmacologie --- chemie --- anorganische chemie
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