The Chemistry of the Akuammiline Alkaloids

Adams, Gregory L.; Smith, Amos B.

doi:10.1016/bs.alkal.2015.08.001

Cited by 28 publications

(41 citation statements)

References 125 publications

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“…The monoterpene indole alkaloid (MIA), lanciferine ( 87a ), was isolated in 1973 from the aerial parts of the New-Caledonian plant, Alstonia boulindaensis Boiteau (Apocynaceae)205 and belongs to the akuammiline family 206. Engendering numerous complex scaffolds, the akuammiline MIAs have received much attention by synthetic chemists owing to their molecular structures and a broad range of biological activities 207.…”

Section: Dereplicationmentioning

confidence: 99%

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

et al. 2019

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Covering: up to 2018With contributions from the global natural product (NP) research community, and continuing the Raw Data Initiative, this review collects a comprehensive demonstration of the immense scientific value of disseminating raw nuclear magnetic resonance (NMR) data, independently of, and in parallel with, classical publishing outlets. A comprehensive compilation of historic to present-day cases as well as contemporary and future applications show that addressing the urgent need for a repository of publicly accessible raw NMR data has the potential to transform natural products (NPs) and associated fields of chemical and biomedical research. The call for advancing open sharing mechanisms for raw data is intended to enhance the transparency of experimental protocols, augment the reproducibility of reported outcomes, including biological studies, become a regular component of responsible research, and thereby enrich the integrity of NP research and related fields.

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Section: Dereplicationmentioning

confidence: 99%

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

et al. 2019

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“…8 Since the milestone syntheses of reserpine and strychnine by Woodward et al in the 1950s, 9,10 the syntheses of complex monoterpenoid indole alkaloids has been an interesting and challenging topic because of their rich structural diversity and biological activities. [11][12][13][14] The Bigger Picture Today, achieving the chemical synthesis of a single natural product is rarely out of reach with sufficient manpower. However, considering the urgent demand for chemical biology studies and drug discovery, efficient preparation of a large collection of complex natural products and natural-product-like libraries with stereochemical and architectural divergence remains highly desirable.…”

Section: Introductionmentioning

confidence: 99%

A Radical Cascade Enabling Collective Syntheses of Natural Products

Wang

Xia

Qin

et al. 2017

Chem

150

107

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Qin and co-workers use photocatalytic conditions to generate a nitrogencentered radical from aniline-type sulfonamide, which reverses the conventional reactivity between two electron-donating amine and enamine groups and initiates radical cascade reactions with excellent chemo-, regio-, and diastereoselectivity. The power of this distinct method has been demonstrated by the efficient syntheses of 33 monoterpenoid indole alkaloids belonging to four families.

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“…Since then, most synthetic works on 2 and the structurally related akuammiline alkaloids have been focused on the construction of the characteristic tetracyclic hydrocarbazole core, such as 9. [16][17][18] Here, we review recent advances in methodologies for the construction of the C4a,C9a-fused tetracyclic hydrocarbazole skeleton (1).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Synthetic Strategies for the C4a,C9a-Fused Tetracyclic Hydrocarbazole Core Structure of Minfiensine and Related Akuammiline Alkaloids

Nagasawa¹,

Odagi²,

Hosoya³

et al. 2021

HETEROCYCLES

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The Strychnos alkaloid minfiensine and its analogs among the akuammiline alkaloids have a variety of biological activities, including anti-tumor and analgesic activities, and have therefore attracted considerable synthetic interest. Here we provide an overview of recent advances in methodologies for the construction of the characteristic tetracyclic hydrocarbazole core structure containing a fused pyrrolidine ring at C4a and C9a.

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The Chemistry of the Akuammiline Alkaloids

Cited by 28 publications

References 125 publications

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

A Radical Cascade Enabling Collective Syntheses of Natural Products

Recent Advances in Synthetic Strategies for the C4a,C9a-Fused Tetracyclic Hydrocarbazole Core Structure of Minfiensine and Related Akuammiline Alkaloids

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