The combination of copper(I) iodide and cesium fluoride significantly enhances the Stille reaction. After extensive optimisation, a variety of electronically unfavourable and sterically hindered substrates were coupled in very high yields under mild conditions.
The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.
The biomimetic synthesis of the manzamine-related alkaloid keramaphidin B is described. The key intramolecular Diels ± Alder reaction proposed in the Baldwin and Whitehead hypothesis is demonstrated. An investigation of the modified biomimetic hypothesis proposed by Marazano et al. is also reported. Finally, an alternative synthesis of keramaphidin B by Grubbs methathesis is presented.
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