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Record Nr. |
UNINA9910420949003321 |
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Autore |
Matsuoka Junpei |
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Titolo |
Total synthesis of indole alkaloids : based on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations / / Junpei Matsuoka |
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Pubbl/distr/stampa |
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Singapore : , : Springer, , [2020] |
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©2020 |
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ISBN |
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Edizione |
[1st ed. 2020.] |
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Descrizione fisica |
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1 online resource (XII, 82 p. 77 illus., 4 illus. in color.) |
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Collana |
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Disciplina |
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Soggetti |
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Indole - Synthesis |
Catalysis |
Chemistry, Inorganic |
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Lingua di pubblicazione |
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Formato |
Materiale a stampa |
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Livello bibliografico |
Monografia |
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Nota di bibliografia |
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Includes bibliographical references. |
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Nota di contenuto |
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1. Introduction -- 2. Total Synthesis of Dictyodendrin A–F by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles -- 3. Construction of the Pyrrolo[2,3-d]carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide. |
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Sommario/riassunto |
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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 |
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alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds. |
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