Biomimetic Macrocycle-Forming Diels−Alder Reaction of an Iminium Dienophile: Synthetic Studies Directed Toward Gymnodimine
Organic Letters2005Vol. 7(18), pp. 3997–4000
Citations Over TimeTop 12% of 2005 papers
Abstract
The macrocyclic core of gymnodimine has been constructed via an intramolecular Diels-Alder reaction of an alpha,beta-unsaturated iminium dienophile in water. The cycloaddition furnished a single exo-product, along with two endo-products. Through X-ray analysis of a suitable derivative, the stereochemistry of the exo-product was established, thereby demonstrating that its stereochemistry matches that of gymnodimine. In contrast, macrocyclization of an analogous alpha,beta-unsaturated ketone dienophile gave only undesired endo-products. Interestingly, the imine dienophile shows remarkable stability in water. [reaction: see text]
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