A novel total synthesis of aculeatin A via a stepwise approach

Zhang, Zhibin; Leng, Xiao; Yang, Shenkun; Cheng, Liang; Huang, Shuangping; Wang, Xiaoji

doi:10.1039/c6ra27140e

Cited by 5 publications

(1 citation statement)

References 34 publications

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“…In Scheme 120, a synthetic approach to antimalarial dispirocyclic aculeatin A ( 120.4 ), extracted from the plant Amomum aculeatum , was depicted in nine steps from 1‐tetradecanal ( 120.1 ). Zhang et al [132] . applied a Crimmins modified Evans aldol reaction with thioxazolidinone moiety 76.9 and aldehyde 120.1 in the presence of TiCl 4 , DIPEA, and NMP to obtain the aldol adduct 120.2 with a 65% overall yield.…”

Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

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Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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Asymmetric Synthesis of Bispiro[γ‐butyrolactone‐pyrrolidin‐4,4′‐pyrazolone] Scaffolds Containing Two Quaternary Spirocenters via an Organocatalytic 1,3‐Dipolar Cycloaddition

et al. 2018

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Enantiomerically enriched bispiro[γ‐butyrolactone‐pyrrolidin‐4,4′‐pyrazolone] skeletons were synthesized firstly through a simple organocatalytic 1,3‐dipolar cycloaddition reaction between α‐imino γ‐lactones and alkylidene pyrazolones in high yields and excellent stereoselectivities. This efficient organocatalytic strategy provides facile access to a variety of highly functionalized drug‐like compounds with two quaternary spirocenters and should allow for structure diversification of this intriguing class of compounds.

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The Search for Anticancer Agents from Tropical Plants

Henkin

Ren

Soejarto

et al. 2018

Progress in the Chemistry of Organic Natural Products

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Many of the clinically used anticancer agents in Western medicine are derived from secondary metabolites found in terrestrial microbes, marine organisms, and higher plants, with additional compounds of this type being currently in clinical trials. If plants are taken specifically, it is generally agreed that the prospects of encountering enhanced small organic-molecule chemical diversity are better if tropical rather than temperate species are investigated in drug discovery efforts. Plant collection in tropical source countries requires considerable preparation and organization to conduct in a responsible manner that abides by the provisions of the 1992 Rio Convention of Biological Diversity and the 2010 Nagoya Protocol on Access to Genetic Resources. Correct taxonomic identifications and enhanced procedures for processing and documenting plant samples when collected in often difficult terrain are required. Phytochemical aspects of the work involve solvent fractionation, known compound dereplication, preliminary in vitro testing, and prioritization, leading to "activity-guided fractionation", compound structure determination, and analog development. Further evaluation of lead compounds requires solubility, formulation, preliminary pharmacokinetics, and in vivo testing in suitable models. Covering the work of the authors carried out in two sequential multidisciplinary, multi-institutional research projects, examples of very promising compounds discovered from plants acquired from Africa, Southeast Asia, the Americas, and the Caribbean region, and with potential anticancer activity will be mentioned. These include plant secondary metabolites of the diphyllin lignan, cyclopenta[b]benzofuran, triterpenoid, and tropane alkaloid types.

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A novel total synthesis of aculeatin A via a stepwise approach

Abstract: Aculeatin A, isolated from the plant Amomum aculeatum, is a dispirocyclic compound having antimalarial activity. We describe a novel synthetic approach to aculeatin A via a stepwise strategy.

Cited by 5 publications

References 34 publications

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Asymmetric Synthesis of Bispiro[γ‐butyrolactone‐pyrrolidin‐4,4′‐pyrazolone] Scaffolds Containing Two Quaternary Spirocenters via an Organocatalytic 1,3‐Dipolar Cycloaddition

The Search for Anticancer Agents from Tropical Plants

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A novel total synthesis of aculeatin A via a stepwise approach

Abstract: Aculeatin A, isolated from the plant Amomum aculeatum, is a dispirocyclic compound having antimalarial activity. We describe a novel synthetic approach to aculeatin A via a stepwise strategy.

Cited by 5 publications

References 34 publications

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Asymmetric Synthesis of Bispiro[γ‐butyrolactone‐pyrrolidin‐4,4′‐pyrazolone] Scaffolds Containing Two Quaternary Spirocenters via an Organocatalytic 1,3‐Dipolar Cycloaddition

The Search for Anticancer Agents from Tropical Plants

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Product

Resources

About

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis