Stereoselective approaches to (E,E,E) and (Z,E,E)-α-chloro-ω-substituted hexatrienes: Synthesis of all E polyenes

Add time:08/25/2019    Source:sciencedirect.com

Two stereocontrolled synthetic approaches to (E,E,E) and (Z,E,E)-α-chloro-ω-substituted hexatrienes 1–3 are described starting from unsaturated compounds 4–6. The key step of the first approach is based on the palladium-catalyzed rearrangement of bis-allylic acetates 4 and 5 and the second one is based on the stereoselective reduction of homopropargylic alcohols 6 followed by an elimination reaction. These stable chlorotrienes 1–3 are suitable synthetic intermediates for the construction of navenone B and all E polyenes (trienes, tetraenes, hexaenes and heptaenes).

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