Abstract
Ellagitannins are a structurally and biologically diverse class of hydrolysable tannins. The structure typically consists of galloyl and hexahydroxydiphenoyl group(s), which are esterified to glucose. A number of biological and pharmacological activities have been reported in this class of natural products. The focus of this review is progress in strategies and methodologies for the total synthesis of ellagitannins. The first half of this review describes the previously achieved total syntheses along with the synthetic problems and solutions including formation of the HHDP-bridge, preparation of dehydrodigalloyl ether, control of anomeric isomers, and protecting groups in the syntheses. The latter half describes the three recent total syntheses of ellagitannins including details of the first synthesis of an axial- rich ellagitannin, of which glucose moiety is in a 1C4 or a twist-boat conformation that has more axially oriented C-O bonds.
Keywords: Ellagitannin, Total synthesis, Synthetic strategy and methodology, Axial-rich
Current Organic Chemistry
Title:Strategies and Methods for the Total Synthesis of Ellagitannins
Volume: 16 Issue: 5
Author(s): Hidetoshi Yamada, Tsukasa Hirokane, Noriaki Asakura, Yusuke Kasai, Kohei Nagao
Affiliation:
Keywords: Ellagitannin, Total synthesis, Synthetic strategy and methodology, Axial-rich
Abstract:
Ellagitannins are a structurally and biologically diverse class of hydrolysable tannins. The structure typically consists of galloyl and hexahydroxydiphenoyl group(s), which are esterified to glucose. A number of biological and pharmacological activities have been reported in this class of natural products. The focus of this review is progress in strategies and methodologies for the total synthesis of ellagitannins. The first half of this review describes the previously achieved total syntheses along with the synthetic problems and solutions including formation of the HHDP-bridge, preparation of dehydrodigalloyl ether, control of anomeric isomers, and protecting groups in the syntheses. The latter half describes the three recent total syntheses of ellagitannins including details of the first synthesis of an axial- rich ellagitannin, of which glucose moiety is in a 1C4 or a twist-boat conformation that has more axially oriented C-O bonds.
Export Options
About this article
Cite this article as:
Hidetoshi Yamada, Tsukasa Hirokane, Noriaki Asakura, Yusuke Kasai, Kohei Nagao , Strategies and Methods for the Total Synthesis of Ellagitannins, Current Organic Chemistry 2012; 16 (5) . https://dx.doi.org/10.2174/138527212799859426
DOI https://dx.doi.org/10.2174/138527212799859426 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements