Abstract
A Simple and General Platform for Generating Stereochemically Complex Polyene Frameworks by Iterative Cross‐Coupling
Highlights
Approach has been realized in the first synthesis of the highly complex (E,E,E,Z,Z,E,E)-heptaene framework of the ion channel-forming polyene macrolide vacidin A
We recently reported three haloalkenyl methyliminodiacetic acid (MIDA) boronates that enabled the preparation of a subset of polyene motifs by iterative cross-coupling (ICC).[2b]. Albeit an important step forward, this collection only provided access to all-trans-polyene substructures and utilized polyenylchlorides
We discovered that (E)-1 and (Z)-1 can both be generated from the novel ethynyl MIDA boronate 6, which in turn can be prepared from readily available Grignard reagent 5.[2h,9] as shown in Scheme 3, the addition of 5 to selective couplings and iododegermylations (Scheme 2 A)
Summary
Approach has been realized in the first synthesis of the highly complex (E,E,E,Z,Z,E,E)-heptaene framework of the ion channel-forming polyene macrolide vacidin A. Enabling stereospecific access to these stereochemically complex polyene frameworks, we describe the development of a novel ICC platform that yields bifunctional iodopolyenyl N-methyliminodiacetic acid (MIDA) boronates in all possible stereoisomeric forms. B) Core building blocks to enable general access to stereoisomeric iodopolyenyl MIDA boronates.
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