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2012 | Buch

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Alkaloid Synthesis

herausgegeben von: Hans-Joachim Knölker

Verlag: Springer Berlin Heidelberg

Buchreihe : Topics in Current Chemistry

Enthalten in: Springer Professional "Wirtschaft+Technik" , Springer Professional "Technik"

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Über dieses Buch

Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-

Inhaltsverzeichnis

Frontmatter

Lycopodium Alkaloids: Isolation and Asymmetric Synthesis

Abstract

Lycopodium alkaloids have attracted the attention of many natural product chemists and synthetic organic chemists due to their important biological activities and unique skeletal characteristics. In this review we describe isolation and asymmetric syntheses of several new alkaloids such as lycoposerramines-C, -V, -W, and cernuine, and show that asymmetric total synthesis played a key role in elucidating the structures of these complex natural products.

Graphical Abstract

Mariko Kitajima, Hiromitsu Takayama

Synthesis of Morphine Alkaloids and Derivatives

Abstract

This review summarizes recent developments in the total synthesis of morphine alkaloids and some of the semisynthetic derivatives. The literature is covered for the period of 5 years after the publication of the last review in 2005. The syntheses that appeared in this period are covered in detail and are placed in the context of all syntheses of opiate alkaloids since the original one published by Gates in 1952. The introduction covers the historical aspects of total synthesis of these alkaloids. The synthesis of some of the medicinally useful derivatives is reviewed in the last section along with some of the methodology required for their preparation.

Graphical Abstract

Uwe Rinner, Tomas Hudlicky

Indole Prenylation in Alkaloid Synthesis

Abstract

Important biologically active indole alkaloids are decorated with prenyl (3,3-dimethylallyl) and tert-prenyl (1,1-dimethylallyl) groups. Covering the literature until the end of 2010, this review article comprehensively summarises and discusses the currently available technologies of prenylation and tert-prenylation of indoles, which have been applied in natural products total syntheses or could be applied there in the near future. We focus on those procedures which introduce the C₅ units in one step, organised according to the indole position to be functionalised. Key strategies include electrophilic and nucleophilic prenylation and tert-prenylation, prenyl and tert-prenyl rearrangements, transition metal-mediated reactions and enzymatic methods.

Thomas Lindel, Nils Marsch, Santosh Kumar Adla

Marine Pyrroloiminoquinone Alkaloids

Abstract

Recent reports on the synthetic studies of marine pyrroloiminoquinone alakloids and their analogs are reviewed.

Yasuyuki Kita, Hiromichi Fujioka

Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids

Abstract

The total syntheses of a wide range of terrestrially derived alkaloids, especially ones isolated from members of the Amaryllidaceae family, are described. Two recurring themes associated with these syntheses are the use of two types of building blocks, namely ring-fused cyclopropanes, especially geminally-dihalogenated ones, and enzymatically derived cis-1,2-dihydrocatechols. These have often served as precursors to 2- or 3-halogenated 2-cyclohexen-1-ols that are themselves engaged in cross-coupling reactions, radical addition-elimination processes and/or Claisen- or Overman-type rearrangements so as to construct the highly functionalized six-membered rings associated with the target alkaloids.

Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz, Lorenzo V. White

Synthesis of Pyrrole and Carbazole Alkaloids

Abstract

An overview of recent transition metal-catalyzed syntheses of pyrroles and carbazoles is presented. The focus is on methods which have been applied to the preparation of biologically active naturally occurring pyrrole and carbazole alkaloids. For pyrroles, special attention is paid to silver(I)-catalyzed cyclization reactions. For carbazoles, iron(0)-mediated and palladium(0/II)-catalyzed cyclization reactions are highlighted and their broad range of applications is discussed.

Graphical Abstract

Ingmar Bauer, Hans-Joachim Knölker

Backmatter

Titel: Alkaloid Synthesis
herausgegeben von: Hans-Joachim Knölker
Verlag: Springer Berlin Heidelberg
Electronic ISBN: 978-3-642-25529-8
Print ISBN: 978-3-642-25528-1
DOI: https://doi.org/10.1007/978-3-642-25529-8

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