The Total Synthesis of Chondrochloren A
Yannick Linne, Elisa Bonandi, Christopher Tabet, Jan Geldsetzer, Markus Kalesse
Abstract
The first total synthesis of chondrochloren A is accomplished using a 1,2-metallate rearrangement addition as an alternative for the Nozaki-Hiyama-Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z-enamide is accomplished using a Z-selective cross coupling of the corresponding amide to a Z-vinyl bromide.
Topics & Concepts
Total synthesisAmidePolyketideVinyl bromideChemistryStereochemistryBromideTransformation (genetics)Combinatorial chemistryCoupling reactionFormal synthesisOrganic chemistryCatalysisBiosynthesisEnzymeBiochemistryGeneSynthetic Organic Chemistry MethodsAxial and Atropisomeric Chirality SynthesisCoordination Chemistry and Organometallics