Photochemical Reactions as Key Steps in Natural Product Synthesis

Photochemical reactions contribute in a significant way to the existing repertoire of carbon–carbon bond‐forming reactions by allowing access to exceptional molecular structures that cannot be obtained by conventional means. In this Review, the most important photochemical transformations that have...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-02, Vol.50 (5), p.1000-1045
Main Authors: Bach, Thorsten, Hehn, Jörg P.
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
cyclization
cycloaddition
Natural products
Photochemical Processes
Photochemical reactions
Photochemicals
photochemistry
Photochemistry - methods
total synthesis
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Summary:Photochemical reactions contribute in a significant way to the existing repertoire of carbon–carbon bond‐forming reactions by allowing access to exceptional molecular structures that cannot be obtained by conventional means. In this Review, the most important photochemical transformations that have been employed in natural product synthesis are presented. Selected total syntheses are discussed as examples, with particular attention given to the photochemical key step and its stereoselectivity. The structural relationship between the photochemically generated molecule and the natural product is shown, and, where necessary, the consecutive reactions in the synthesis are illustrated and classified. Squaring the circle: The total syntheses of natural products can often be achieved by means of a photochemical key step. Photochemical reactions, like few other reactions, allow the stereoselective syntheses of complex carbon skeletons, thus providing elegant access to comprehensive target molecules (see examples).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201002845