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Total synthesis of indole alkaloidsb...

Matsuoka, Junpei.

Total synthesis of indole alkaloidsbased on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /

Record Type:	Electronic resources : Monograph/item
Title/Author:	Total synthesis of indole alkaloidsby Junpei Matsuoka.
Reminder of title:	based on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /
Author:	Matsuoka, Junpei.
Published:	Singapore :Springer Singapore :2020.
Description:	xii, 82 p. :ill., digital ;24 cm.
Contained By:	Springer Nature eBook
Subject:	Indole alkaloidsSynthesis.
Online resource:	https://doi.org/10.1007/978-981-15-8652-1
ISBN:	9789811586521$q(electronic bk.)

Total synthesis of indole alkaloidsbased on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /
Matsuoka, Junpei.

Total synthesis of indole alkaloidsbased on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /[electronic resource] :by Junpei Matsuoka. - Singapore :Springer Singapore :2020. - xii, 82 p. :ill., digital ;24 cm. - Springer theses,2190-5053. - Springer theses..

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.

ISBN: 9789811586521$q(electronic bk.)

Standard No.: 10.1007/978-981-15-8652-1doiSubjects--Topical Terms:

877128
Indole alkaloids
--Synthesis.

LC Class. No.: QP801.I45

Dewey Class. No.: 572.549

Total synthesis of indole alkaloidsbased on direct construction of pyrrolocarbazole scaffolds via gold-catalyzed cascade cyclizations /
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505 0 $a 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.
520 $a 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.
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