Highly Efficient and General Synthetic Method of Various Retinyl Ethers

Jun Sup Lee; Young Cheol Jeong; Minkoo Ji; Woonphil Baik; Sijoon Lee; Sangho Koo

doi:10.1055/s-2004-830873

LETTER

Highly Efficient and General Synthetic Method of Various Retinyl Ethers

Jun Sup Lee^a, Young Cheol Jeong^a, Minkoo Ji^a, Woonphil Baik^a, Sijoon Lee^b, Sangho Koo*^a
^a Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea
Fax: +82(31)3357248; e-Mail: sangkoo@mju.ac.kr;
^b Chemical Research Center, SK Corporation, Yusung, Taejon, 305-370, Korea

Abstract

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Abstract

Bromination of 4 by PBr₃ 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 C₅ allylic chloride 3. The Julia olefination reaction with the C₁₅ sulfone 2 provides diverse retinyl ethers 1.

Key words

retinyl ethers - olefination - stereoselective synthesis - sulfones - vitamins

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References

<A NAME="RU13504ST-1A">1a</A> Jaeger EP. Jurs PC. Stouch TR. Eur. J. Med. Chem. 1993, 28: 275

<A NAME="RU13504ST-1B">1b</A> Newton DL. Henderson WR. Sporn MB. Cancer Res. 1980, 40: 3413

<A NAME="RU13504ST-2">2</A> Bard DR. Lasnitzki I. Br. J. Cancer 1977, 35: 115

<A NAME="RU13504ST-3">3</A> Sporn MB. Dunlop NM. Newton DL. Henderson WR. Nature 1976, 263: 110

<A NAME="RU13504ST-4A">4a</A> Agadir A. Shealy YF. Hill DL. Zhang X.-K. Cancer Res. 1997, 57: 3444

<A NAME="RU13504ST-4B">4b</A> McPhillips DM. Lindamood C. Heath JE. Hill DL. Drug Metab. Dispos. 1988, 16: 683

<A NAME="RU13504ST-4C">4c</A> Grubbs CJ. Moon RC. Sporn MB. Newton DL. Cancer Res. 1977, 37: 599

<A NAME="RU13504ST-5">5</A> Kienzle F. Helv. Chim. Acta 1973, 56: 1662

<A NAME="RU13504ST-6">6</A> Shealy YF. Frye JL. Riordan JM. Hill DL. McPhillips M. Wille JJ. Sani BP. Kalin JR. Eto I. Grubbs CJ. Anti-Cancer Drug Des. 1997, 12: 15

<A NAME="RU13504ST-7A">7a</A> Julia M. Paris J.-M. Tetrahedron Lett. 1973, 4833

<A NAME="RU13504ST-7B">7b</A> Julia M. Arnould D. Bull. Soc. Chim. Fr. 1973, 743

<A NAME="RU13504ST-7C">7c</A> Julia M. Launay M. Stacino J.-P. Verpeaux J.-N. Tetrahedron Lett. 1982, 23: 2465

<A NAME="RU13504ST-7D">7d</A> Bremner J. Julia M. Launay M. Stacino J.-P. Tetrahedron Lett. 1982, 23: 3265

<A NAME="RU13504ST-8">8</A> Manchand PS. Rosenberger M. Saucy G. Wehrli PA. Wong H. Chambers L. Ferro MP. Jackson W. Helv. Chim. Acta 1976, 59: 387

<A NAME="RU13504ST-9A">9a</A> Choi H. Ji M. Park M. Yun I.-K. Oh S.-S. Baik W. Koo S. J. Org. Chem. 1999, 64: 8051

<A NAME="RU13504ST-9B">9b</A> Ji M. Choi H. Park M. Kee M. Jeong YC. Koo S. Angew. Chem. Int. Ed. 2001, 40: 3627

<A NAME="RU13504ST-9C">9c</A> Ji M. Choi H. Jeong YC. Jin J. Baik W. Lee S. Kim JS. Park M. Koo S. Helv. Chim. Acta 2003, 86: 2620

<A NAME="RU13504ST-10A">10a</A> Julia M. Arnould D. Bull. Soc. Chim. Fr. 1973, 746

<A NAME="RU13504ST-10B">10b</A> Chabardes P. Decor JP. Varagnat J. Tetrahedron 1977, 33: 2799

<A NAME="RU13504ST-11A">11a</A> Oroshnik W. Mallory RA. J. Am. Chem. Soc. 1950, 72: 4608

<A NAME="RU13504ST-11B">11b</A> Heasley VL. Chamberlain PH. J. Org. Chem. 1970, 35: 539

<A NAME="RU13504ST-12">12</A> Bäckvall J.-E. Nyström J.-E. Nordberg RE. J. Am. Chem. Soc. 1985, 107: 3676

<A NAME="RU13504ST-13">13</A> Dalton DR. Dutta VP. Jones DC. J. Am. Chem. Soc. 1968, 90: 5498

<A NAME="RU13504ST-14">14</A> Corey EJ. Noe MC. Shieh WC. Tetrahedron Lett. 1993, 34: 5995

<A NAME="RU13504ST-15">15</A> Julia M. Deprez D. Tetrahedron Lett. 1976, 277

Decomposition of the NMR sample of retinyl acetate in CDCl₃ at ambient temperature was noticed within one week.