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Research paper thumbnail of ChemInform Abstract: Green Oxidation of Furans - Initiated by Molecular Oxygen - that Give Key Natural Product Motifs

Research paper thumbnail of Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds

Research paper thumbnail of Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC-ring motif of the pectenotoxins

Chemical Communications, 2011

The key ABC-ring motif of the pectenotoxins has been synthesized, starting from a simple and read... more The key ABC-ring motif of the pectenotoxins has been synthesized, starting from a simple and readily accessible difuran precursor, using a complex singlet oxygen-mediated cascade reaction sequence.

Research paper thumbnail of A Versatile Synthesis of Meyers’ Bicyclic Lactams from Furans: Singlet-Oxygen-Initiated Reaction Cascade

Angewandte Chemie International Edition, 2012

A new and powerful method for the synthesis Meyers' bicyclic lactams beginning from furans is rep... more A new and powerful method for the synthesis Meyers' bicyclic lactams beginning from furans is reported herein that uses a remarkable one-pot singlet oxygen-initiated cascade reaction sequence to deliver the corresponding bicyclic lactams in high yield. Ever since they were pioneered Meyers' homochiral bicyclic lactams [1, 2] (B, Scheme 1) have been exceedingly popular and versatile scaffolds for the enantioselective construction of new stereogenic centres, including the most challenging typequaternary carbon centres. They have been utilised in myriad different ways to target a wide variety of natural products, [2, 3] nonnatural molecules possessing interesting biological activity, [2, 4] and, also in a diverse array of other synthetic endeavours. [2, 5] The most general method for their synthesis, introduced in the seminal work of Meyers', [1, 2] wherein a γ-ketoacid is condensed with an aminoalcohol under dehydrating conditions in refluxing toluene, is still, by far, the most commonly employed means of accessing the bicyclic scaffold B. Modifications have been made with the aim of introducing milder variants [6] to the Meyers' lactamisation; these Scheme 1. Generalised representation of the transformation achieved with this new methodology.

Research paper thumbnail of Green oxidations of furans—initiated by molecular oxygen—that give key natural product motifs

Organic & Biomolecular Chemistry, 2011

In this article, we explore how changes in the positioning of pendant hydroxyl functionalities in... more In this article, we explore how changes in the positioning of pendant hydroxyl functionalities in the photooxygenation substrate dramatically alter the course of furan oxidations that are initiated by singlet oxygen; and, how these different reactivities can be harnessed through cascade reaction sequences to access, rapidly and effectively, a broad range of important natural product motifs.

Research paper thumbnail of ChemInform Abstract: Green Oxidation of Furans - Initiated by Molecular Oxygen - that Give Key Natural Product Motifs

Research paper thumbnail of Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds

Research paper thumbnail of Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC-ring motif of the pectenotoxins

Chemical Communications, 2011

The key ABC-ring motif of the pectenotoxins has been synthesized, starting from a simple and read... more The key ABC-ring motif of the pectenotoxins has been synthesized, starting from a simple and readily accessible difuran precursor, using a complex singlet oxygen-mediated cascade reaction sequence.

Research paper thumbnail of A Versatile Synthesis of Meyers’ Bicyclic Lactams from Furans: Singlet-Oxygen-Initiated Reaction Cascade

Angewandte Chemie International Edition, 2012

A new and powerful method for the synthesis Meyers' bicyclic lactams beginning from furans is rep... more A new and powerful method for the synthesis Meyers' bicyclic lactams beginning from furans is reported herein that uses a remarkable one-pot singlet oxygen-initiated cascade reaction sequence to deliver the corresponding bicyclic lactams in high yield. Ever since they were pioneered Meyers' homochiral bicyclic lactams [1, 2] (B, Scheme 1) have been exceedingly popular and versatile scaffolds for the enantioselective construction of new stereogenic centres, including the most challenging typequaternary carbon centres. They have been utilised in myriad different ways to target a wide variety of natural products, [2, 3] nonnatural molecules possessing interesting biological activity, [2, 4] and, also in a diverse array of other synthetic endeavours. [2, 5] The most general method for their synthesis, introduced in the seminal work of Meyers', [1, 2] wherein a γ-ketoacid is condensed with an aminoalcohol under dehydrating conditions in refluxing toluene, is still, by far, the most commonly employed means of accessing the bicyclic scaffold B. Modifications have been made with the aim of introducing milder variants [6] to the Meyers' lactamisation; these Scheme 1. Generalised representation of the transformation achieved with this new methodology.

Research paper thumbnail of Green oxidations of furans—initiated by molecular oxygen—that give key natural product motifs

Organic & Biomolecular Chemistry, 2011

In this article, we explore how changes in the positioning of pendant hydroxyl functionalities in... more In this article, we explore how changes in the positioning of pendant hydroxyl functionalities in the photooxygenation substrate dramatically alter the course of furan oxidations that are initiated by singlet oxygen; and, how these different reactivities can be harnessed through cascade reaction sequences to access, rapidly and effectively, a broad range of important natural product motifs.