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

Departament de Química

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8 Cites (Scopus)

Resum

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.

Idioma original	Anglès
Pàgines (de-a)	2493-2499
Revista	Tetrahedron
Volum	37
Número	14
DOIs	https://doi.org/10.1016/S0040-4020(01)88908-0
Estat de la publicació	Publicada - 1 de gen. 1981

Accés al document

10.1016/S0040-4020(01)88908-0

Altres arxius i enllaços

https://www.scopus.com/pages/publications/0342659509

Com citar-ho

@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",

volume = "37",

pages = "2493--2499",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "14",

}

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.

UR - https://www.scopus.com/pages/publications/0342659509

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

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

M3 - Article

SN - 0040-4020

VL - 37

SP - 2493

EP - 2499

JO - Tetrahedron

JF - Tetrahedron

IS - 14