Stereoselective Synthesis of the Octahydronaphthalene Unit of Integramycin via an Intramolecular Diels−Alder Reaction
Organic Letters2005Vol. 7(7), pp. 1355–1358
Citations Over TimeTop 11% of 2005 papers
Abstract
[reaction: see text] The racemic cis-decalin core fragment 30 of integramycin was synthesized by a sequence involving a highly diastereoselective intramolecular Diels-Alder reaction of triene 24. A remarkable switch in stereoselectivity occurred upon changing the dienophile unit of 24 from (Z)- to (E)-geometry.
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