Synlett

Highly efficient and general synthetic method of various retinyl ethers

JS Lee, YC Jeong, M Ji, W Baik, S Lee, S Koo

Index: Lee, Jun Sup; Jeong, Young Cheol; Ji, Minkoo; Baik, Woonphil; Lee, Sijoon; Koo, Sangho Synlett, 2004 , # 11 p. 1937 - 1940

Full Text: HTML

Citation Number: 2

Abstract

Abstract Bromination of 4 by PBr 3 under Cu I catalyst produces the ambidextrous allylic halide 5 regioselectively and stereoselectively. Hetero nucleophiles distinguish the allylic carbon containing Br from the one containing Cl in 5 to give the heteroatom-substituted C 5 allylic chloride 3. The Julia olefination reaction with the C 15 sulfone 2 provides diverse retinyl ethers 1.

 Related Synthetic Route
Potassium acetate Structure

127-08-2

Potassium acetate

(E)-4-Bromo-1-chloro-2-methyl-2-butene Structure

114506-04-6

(E)-4-Bromo-1-c...

~94%

acetic acid,4-chloro-3-methylbut-2-en-1-ol Structure

24529-80-4

acetic acid,4-c...

9-(2,6,6-Trimethyl-cyclohex-1-enyl)-5-phenyl-sulphonyl-3,7-dimethyl-1-acetoxy-nona-2,6,8-triene Structure

50465-60-6

9-(2,6,6-Trimet...

~96%

Vitamin A Structure

68-26-8

Vitamin A

(((2E,6E,8E)-3,7-dimethyl-5-(phenylsulfonyl)-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,6,8-trien-1-yl)oxy)benzene Structure

791102-84-6

(((2E,6E,8E)-3,...

~83%

[(2Z,4Z,6Z,8Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]benzene Structure

75664-68-5

[(2Z,4Z,6Z,8Z)-...

N/A Structure

38987-91-6

N/A

~%

[(2Z,4Z,6Z,8Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]benzene Structure

75664-68-5

[(2Z,4Z,6Z,8Z)-...

(E)-4-Bromo-1-chloro-2-methyl-2-butene Structure

114506-04-6

(E)-4-Bromo-1-c...

~%

[(2Z,4Z,6Z,8Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]benzene Structure

75664-68-5

[(2Z,4Z,6Z,8Z)-...

Phenol Structure

108-95-2

Phenol

~%

[(2Z,4Z,6Z,8Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]benzene Structure

75664-68-5

[(2Z,4Z,6Z,8Z)-...

(E)-((4-chloro-3-methylbut-2-en-1-yl)oxy)benzene Structure

791102-78-8

(E)-((4-chloro-...

~%

[(2Z,4Z,6Z,8Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]benzene Structure

75664-68-5

[(2Z,4Z,6Z,8Z)-...

2-((2E,6E,8E)-3,7-dimethyl-5-(phenylsulfonyl)-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,6,8-trien-1-yl)isoindoline-1,3-dione Structure

791102-86-8

2-((2E,6E,8E)-3...

~89%

2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl]isoindole-1,3-dione Structure

43219-26-7

2-[(2E,4E,6E,8E...

N/A Structure

38987-91-6

N/A

~%

2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl]isoindole-1,3-dione Structure

43219-26-7

2-[(2E,4E,6E,8E...

Potassium phthalimide Structure

1074-82-4

Potassium phtha...

~%

2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl]isoindole-1,3-dione Structure

43219-26-7

2-[(2E,4E,6E,8E...

(E)-4-Bromo-1-chloro-2-methyl-2-butene Structure

114506-04-6

(E)-4-Bromo-1-c...

~%

2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl]isoindole-1,3-dione Structure

43219-26-7

2-[(2E,4E,6E,8E...

(E)-2-(4-chloro-3-methylbut-2-en-1-yl)isoindoline-1,3-dione Structure

791102-79-9

(E)-2-(4-chloro...

~%

2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl]isoindole-1,3-dione Structure

43219-26-7

2-[(2E,4E,6E,8E...

isoprene Structure

78-79-5

isoprene

~78%

1-chloro-2-methylbut-3-en-2-ol Structure

7437-62-9

1-chloro-2-meth...

N/A Structure

50465-62-8

N/A

~85%

2-[(1E,3E,5E,7E)-9-methoxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-1,3,3-trimethylcyclohexene Structure

32450-56-9

2-[(1E,3E,5E,7E...

N/A Structure

38987-91-6

N/A

~%

2-[(1E,3E,5E,7E)-9-methoxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-1,3,3-trimethylcyclohexene Structure

32450-56-9

2-[(1E,3E,5E,7E...

(E)-1-chloro-4-methoxy-2-methyl-but-2-ene Structure

57513-10-7

(E)-1-chloro-4-...

~%

2-[(1E,3E,5E,7E)-9-methoxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-1,3,3-trimethylcyclohexene Structure

32450-56-9

2-[(1E,3E,5E,7E...

(E)-4-Bromo-1-chloro-2-methyl-2-butene Structure

114506-04-6

(E)-4-Bromo-1-c...

~%

2-[(1E,3E,5E,7E)-9-methoxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-1,3,3-trimethylcyclohexene Structure

32450-56-9

2-[(1E,3E,5E,7E...


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