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ChemInform Abstract: Stereoselective Approaches to (E,E,E) and (Z,E,E)-α-Chloro-ω-Substituted Hexatrienes: Synthesis of all-E Polyenes.

✍ Scribed by Benoit Crousse; Margarita Mladenova; Pascal Ducept; Mouad Alami; Gerard Linstrumelle

Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

carboxylic acid esters carboxylic acid esters (acyclic compounds) P 0360

34 -100

Stereoselective Approaches to (E,E,E) and (Z,E,E)-α-Chloro-ω-Substituted Hexatrienes: Synthesis of all-E Polyenes.

-Two efficient procedures for the synthesis of conjugated chlorotrienes are reported. The key step in the first route is the Pd-catalyzed rearrangement of bisallylic acetates. The second one is achieved via stereoselective reduction of homopropargylic alcohols and subsequent elimination. The chlorotrienes are potent precursors of all-E polyenes and navenone B (XIII), a pheromone of the mollusc Navamax inermis.

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