LEADER 03012nam 2200517 450 001 9910420949003321 005 20210217120420.0 010 $a981-15-8652-7 024 7 $a10.1007/978-981-15-8652-1 035 $a(CKB)4100000011457931 035 $a(DE-He213)978-981-15-8652-1 035 $a(MiAaPQ)EBC6353504 035 $a(PPN)250221578 035 $a(EXLCZ)994100000011457931 100 $a20210217d2020 uy 0 101 0 $aeng 135 $aurnn|008mamaa 181 $ctxt$2rdacontent 182 $cc$2rdamedia 183 $acr$2rdacarrier 200 10$aTotal synthesis of indole alkaloids $ebased on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /$fJunpei Matsuoka 205 $a1st ed. 2020. 210 1$aSingapore :$cSpringer,$d[2020] 210 4$dİ2020 215 $a1 online resource (XII, 82 p. 77 illus., 4 illus. in color.) 225 1 $aSpringer theses 311 $a981-15-8651-9 320 $aIncludes bibliographical references. 327 $a1. 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. 330 $aThis book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. The book first describes the total and formal synthesis of dictyodendrins A?F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds. 410 0$aSpringer theses. 606 $aIndole$xSynthesis 606 $aCatalysis 606 $aChemistry, Inorganic 615 0$aIndole$xSynthesis. 615 0$aCatalysis. 615 0$aChemistry, Inorganic. 676 $a547.593 700 $aMatsuoka$b Junpei$0899933 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910420949003321 996 $aTotal synthesis of indole alkaloids$92010771 997 $aUNINA