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ChemInform Abstract: The Utility of the Homo Diels—Alder Reaction in the Synthesis of Natural Product Skeletons: A Cycloaddition—Fragmentation—Cyclization Sequence to Diquinanes and Triquinanes.

✍ Scribed by M. LAUTENS; J. BLACKWELL

Publisher: John Wiley and Sons
Year: 2010
Weight: 39 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199830087

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✦ Synopsis

The Utility of the Homo Diels-Alder Reaction in the Synthesis of Natural Product Skeletons: A Cycloaddition-Fragmentation-Cyclization Sequence to Diquinanes and Triquinanes.

-Adducts such as (I) and (V) derived from Ni-catalyzed homo Diels-Alder reactions undergo a regio-and stereocontrolled mercury-induced cleavage of the cyclopropane ring, providing products such as (II) and (VII). These are useful precursors for the preparation of di-and triquinane systems.

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