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Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 1: Assembly of the acyclic substrates

✍ Scribed by András Toró; Yuan Wang; Pierre Deslongchamps

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
228 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Synthesis of three generations of model substrates with advancing similarity to chatancin are presented. In the first two generations, an Ireland-Ciaisen based six-step sequence supplied the trans-dienophile to be connected by dithiane chemistry to furfurals. In the third generation, a homogeraniol based dienophile aldehyde was coupled with a dilithiated 3-furoic acid. Subsequently, all three generations were concluded with similar functional group modifications as a preparation for a malonate-furyl chloride based macrocyclization.

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