Synthetic Studies of Biomimetic Diels-Alder Processes toward the Helicterin Family of Natural Products

Although the [2.2.2]‐bicyclooctene core of the helicterin, helisorin, and helisterculin class of neolignan natural products could conceivably arise in Nature via Diels–Alder reactions, synthetic explorations have revealed that only under very non‐biomimetic conditions can such cycloadditions be perf...

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Bibliographic Details
Published in:Israel journal of chemistry 2011-04, Vol.51 (3-4), p.378-390
Main Authors: Snyder, Scott A., Kontes, Ferenc
Format: Article
Language:English
Subjects:
biomimetic
Collection
Cycloaddition
Diels-Alder
Diels-Alder reactions
Metabolites
Natural products
oligomers
total synthesis
Viability
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Summary:Although the [2.2.2]‐bicyclooctene core of the helicterin, helisorin, and helisterculin class of neolignan natural products could conceivably arise in Nature via Diels–Alder reactions, synthetic explorations have revealed that only under very non‐biomimetic conditions can such cycloadditions be performed. In this article, we provide a personal account of explorations towards this natural product family, sharing some additional unpublished synthetic work to test the viability of an alternate, Diels–Alder‐based, biogenetic hypothesis for the generation of this unique collection of secondary metabolites.
ISSN:0021-2148
1869-5868
DOI:10.1002/ijch.201100004