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

doi:10.1016/S0040-4020(01)88908-0

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

Department of Chemistry

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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 language	English
Pages (from-to)	2493-2499
Journal	Tetrahedron
Volume	37
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4020(01)88908-0
Publication status	Published - 1 Jan 1981

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@article{903751653b7f4ac1a4d115e2daa67db4,

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

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. {\textcopyright} 1981.",

author = "J. Camps and J. Font and {de March}, P.",

year = "1981",

month = jan,

day = "1",

doi = "10.1016/S0040-4020(01)88908-0",

language = "English",

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pages = "2493--2499",

journal = "Tetrahedron",

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TY - JOUR

T1 - ω-Bromoalkapolyenylmethyl ketones-II. Use of 5-bromo-3-penten-2-one ethylene ketal as a c5-synthon

AU - Camps, J.

AU - Font, J.

AU - de March, P.

PY - 1981/1/1

Y1 - 1981/1/1

N2 - 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.

AB - 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.

U2 - 10.1016/S0040-4020(01)88908-0

DO - 10.1016/S0040-4020(01)88908-0

M3 - Article

VL - 37

SP - 2493

EP - 2499

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 14

ER -

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

Abstract

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