Tetrahedron

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

…, M Mladenova, P Ducept, M Alami, G Linstrumelle

Index: Crousse, Benoit; Mladenova, Margarita; Ducept, Pascal; Alami, Mouad; Linstrumelle, Gerard Tetrahedron, 1999 , vol. 55, # 14 p. 4353 - 4368

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Citation Number: 27

Abstract

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 ...

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