Stereocontrolled Synthesis of Paracentrone

The allene functionality has participated in one of the most exciting voyages in organic chemistry, from chemical curiosities to a recurring building block in modern organic chemistry. In the last decades, a special kind of allene, namely, allenol, has emerged. Allenols, formed by an allene moiety and a hydroxyl functional group with diverse connectivity, have become common building blocks for the synthesis of a wide range of structures and frequent motif in naturally occurring systems. The synergistic effect of the allene and hydroxyl functional groups enables allenols to be considered as a unique and sole functionality exhibiting a special reactivity. This Review summarizes the most significant contributions to the chemistry of allenols that appeared during the past decade, with emphasis on their synthesis, reactivity, and occurrence in natural products.

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Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Alonso

Almendros

2021

Chem. Rev.

143

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Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds

et al. 2020

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Stereocontrolled Synthesis of 19′-Deoxyperidinin

et al. 2018

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The stereocontrolled convergent synthesis of 19'-deoxyperidinin, 2, which might be a useful peridinin analog to understand the ICT characteristics, was efficiently achieved by sequential Pd-catalyzed cross-coupling reactions using bidirectionally extensible conjugated C5 olefin segments. The crucial 5(2H)-ylidenedihydrofuran function of 2 was successfully constructed by the Au-catalyzed regio- and stereoselective 5-exo-dig etherification.

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Stereocontrolled Synthesis of Paracentrone

Cited by 5 publications

References 10 publications

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds

Stereocontrolled Synthesis of 19′-Deoxyperidinin

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