03012nam 2200517 450 991042094900332120210217120420.0981-15-8652-710.1007/978-981-15-8652-1(CKB)4100000011457931(DE-He213)978-981-15-8652-1(MiAaPQ)EBC6353504(PPN)250221578(EXLCZ)99410000001145793120210217d2020 uy 0engurnn|008mamaatxtrdacontentcrdamediacrrdacarrierTotal synthesis of indole alkaloids based on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /Junpei Matsuoka1st ed. 2020.Singapore :Springer,[2020]©20201 online resource (XII, 82 p. 77 illus., 4 illus. in color.) Springer theses981-15-8651-9 Includes bibliographical references.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.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.Springer theses.IndoleSynthesisCatalysisChemistry, InorganicIndoleSynthesis.Catalysis.Chemistry, Inorganic.547.593Matsuoka Junpei899933MiAaPQMiAaPQMiAaPQBOOK9910420949003321Total synthesis of indole alkaloids2010771UNINA