ω-Bromoalkapolyenylmethyl ketones-II. Use of 5-bromo-3-penten-2-one ethylene ketal as a c5-synthon

J. Camps, J. Font, P. de March

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8 Citations (Scopus)

Abstract

The preparation of the phosphonium salt and the dimethyl-phosphonate of (E)-5-bromo-3-penten-2-one ethylene ketal, 6 and 7, is described. These C5-isoprenoid synthons were condensed with several aldehydes and ketones giving mixtures of the corresponding E and Z-olefination products. Reaction of the anion of the phosphonate derivative with β-ionone gave 9-cis and 9-trans-β-C18-tetraenone ketals, 13 and 14, which by subsequent hydrolysis afforded 9-cis and 9-tras-β-C18-tetraenones, 15 and 16. A C8-isoprenoid synthon is also described. © 1981.
Original languageEnglish
Pages (from-to)2493-2499
JournalTetrahedron
Volume37
Issue number14
DOIs
Publication statusPublished - 1 Jan 1981

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