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On the use of unsymmetrically substituted furans in the furan-carbonyl photocycloaddition reaction: Synthesis of a kadsurenone-ginkgolide hybrid

✍ Scribed by Stuart L. Schreiber; Didier Desmaele; John A. Porco Jr.

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
242 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Paterno-Buchi cycloaddition of aldehydes to silyl and stannyl substituted furans has been investigated.

An application of this method to a short synthesis of a hybrid of two inhibitors of platelet activating factor (paf) receptor binding is described.

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Reaction of an isocyanide with an iminium ion intermediate, formed by reaction between an electronpoor 2-hydroxybenzaldehyde derivative and a secondary amine in the presence of silica gel proceeds smoothly at room temperature to afford benzo[b]furan derivatives in high yields.