Traceless Solid Phase Synthesis with Polystyrene-Bound Tellurium and in Comparison with Polystyrene-Bound Selenium

Thomas Ruhland; Jakob Torang; Henrik Pedersen; Jens Christian Madsen; Kia Svane Bang

doi:10.1055/s-2004-831202

PAPER

Traceless Solid Phase Synthesis with Polystyrene-Bound Tellurium and in Comparison with Polystyrene-Bound Selenium

Thomas Ruhland*, Jakob Torang, Henrik Pedersen, Jens Christian Madsen, Kia Svane Bang
Medicinal Chemistry Research, H. Lundbeck A/S, 9 Ottiliavej, 2500 Valby, Denmark
Fax: +4536438237; e-Mail: tr@lundbeck.com;

Abstract

Alle Artikel dieser Rubrik

Abstract

A novel traceless linking strategy by use of polystyrene-bound tellurium is described. The application of the tellurium linker is demonstrated by the solid phase synthesis of a small library of single alkyl aryl ethers containing two points of diversity. Polystyrene-bound tellurium and polystyrene-bound selenium are compared by their cleavage performance under radical conditions (homolysis) at different temperatures. In addition, polystyrene- bound substrates were analysed by the use of high-resolution magic angle spinning (HR-MAS) NMR spectroscopy.

Key words

combinatorial chemistry - solid phase synthesis - traceless linker - polystyrene-bound chalcogenes - HR-MAS NMR spectroscopy

Volltext

Referenzen

References

<A NAME="RZ09304SS-1A">1a</A> Dolle RE. J. Comb. Chem. 2000, 3: 477

<A NAME="RZ09304SS-1B">1b</A> Willoughby CA. Berk SC. Rosauer KG. Degrado S. Chapman KT. Gould SL. Springer MS. Malkowitz L. Schleif WA. Hazuda D. Miller M. Kessler J. Danzeisen R. Holmes K. Lineberger J. Carella A. Carver G. Emini EA. Bioorg. Med. Chem. Lett. 2001, 11: 3137

<A NAME="RZ09304SS-1C">1c</A> Willoughby CA. Hutchins SM. Rosauer KG. Dhar MJ. Chapman KT. Chicchi GG. Sadowski S. Weinberg DH. Patel S. Malkowitz L. Di Salvo J. Pacholok SG. Cheng K. Bioorg. Med. Chem. Lett. 2002, 12: 93

<A NAME="RZ09304SS-1D">1d</A> Shaw D. Chicchi GG. Elliott JM. Kurtz M. Morrison D. Ridgill MP. Szeto N. Watt AP. Williams AR. Swain CJ. Bioorg. Med. Chem. Lett. 2001, 11: 3031

<A NAME="RZ09304SS-2A">2a</A> Bräse S. Dahmen S. Chem.-Eur. J. 2000, 6: 1899

<A NAME="RZ09304SS-2B">2b</A> Comely AC. Gibson SE. Angew. Chem. Int. Ed. 2001, 40: 1012

<A NAME="RZ09304SS-2C">2c</A> Bräse S. Dahmen S. Comb. Chem. Nicolaou KC. Hanko R. Hartwig W. VCH; Weinheim: 2002. Chap. 4.

<A NAME="RZ09304SS-3">3</A> Ruhland T. Andersen K. Pedersen H. J. Org. Chem. 1998, 63: 9204

<A NAME="RZ09304SS-4A">4a</A> Nicolaou KC. Pastor J. Barluenga S. Winssinger N. Chem. Commun. 1998, 1947

<A NAME="RZ09304SS-4B">4b</A> Nicolaou KC. Pfefferkorn JA. Cao G.-Q. Kim S. Kessabi J. Org. Lett. 1999, 1: 807

<A NAME="RZ09304SS-4C">4c</A> Nicolaou KC. Roecker AJ. Pfefferkorn JA. Cao G.-Q. J. Am. Chem. Soc. 2000, 122: 2966

<A NAME="RZ09304SS-4D">4d</A> Nicolaou KC. Pfefferkorn JA. Roecker AJ. Cao G.-Q. Barluenga S. Mitchell HJ. J. Am. Chem. Soc. 2000, 122: 9939

<A NAME="RZ09304SS-4E">4e</A> Nicolaou KC. Pfefferkorn JA. Mitchell HJ. Roecker AJ. Barluenga S. Cao G.-Q. Affleck RL. Lillig JE. J. Am. Chem. Soc. 2000, 122: 9954

<A NAME="RZ09304SS-4F">4f</A> Nicolaou KC. Pfefferkorn JA. Cao G.-Q. Angew. Chem. Int. Ed. 2000, 39: 734

<A NAME="RZ09304SS-4G">4g</A> Nicolaou KC. Cao G.-Q. Pfefferkorn JA. Angew. Chem. Int. Ed. 2000, 39: 739

<A NAME="RZ09304SS-4H">4h</A> Nicolaou KC. Winssinger N. Hughes R. Smethurst C. Cho SY. Angew. Chem. Int. Ed. 2000, 39: 1084

<A NAME="RZ09304SS-4I">4i</A> Nicolaou KC. Mitchell HJ. Fylaktakidou KC. Suzuki H. Rodríguez RM. Angew. Chem. Int. Ed. 2000, 39: 1089

<A NAME="RZ09304SS-4J">4j</A> Nicolaou KC. Cho SY. Hughes R. Winssinger N. Smethurst C. Labischinski H. Endermann R. Chem.-Eur. J. 2001, 7: 3798

<A NAME="RZ09304SS-5A">5a</A> Fujita K. Watanabe K. Oishi A. Ikeda Y. Tagushi Y. Synlett 1999, 1760

<A NAME="RZ09304SS-5B">5b</A> Qian H. Huang X. Synlett 2001, 1913

<A NAME="RZ09304SS-5C">5c</A> Huang X. Sheng S.-R. Tetrahedron Lett. 2001, 42: 9035

<A NAME="RZ09304SS-5D">5d</A> Qian H. Shao L.-X. Huang X. Synlett 2001, 1571

<A NAME="RZ09304SS-5E">5e</A> Horikawa E. Kodaka M. Nakahara Y. Okuno H. Nakamura K. Tetrahedron Lett. 2001, 42: 8337

<A NAME="RZ09304SS-5F">5f</A> Huang X. Sheng S.-R. J. Comb. Chem. 2003, 5: 273

<A NAME="RZ09304SS-5G">5g</A> Nakamura K. Ohnishi Y. Horikawa E. Konakahara T. Kodaka M. Okuno H. Tetrahedron Lett. 2003, 44: 5445

<A NAME="RZ09304SS-5H">5h</A> Qian H. Huang X. J. Comb. Chem. 2003, 5: 569

<A NAME="RZ09304SS-5I">5i</A> Sheng S.-R. Wang X.-C. Liu X.-L. Song C.-S. Synth. Commun. 2003, 33: 2867

<A NAME="RZ09304SS-5J">5j</A> Huang X. Xu W.-M. Org. Lett. 2003, 5: 4649

<A NAME="RZ09304SS-6">6</A> Zaragoza F. Angew. Chem. Int. Ed. 2000, 39: 2077

<A NAME="RZ09304SS-7A">7a</A> Neumann WP. Synthesis 1987, 665

<A NAME="RZ09304SS-7B">7b</A> Clive DLJ. Chittattu GJ. Farina V. Kiel WA. Menchen SM. Russell CG. Singh A. Wong CK. Curtis NJ. J. Am. Chem. Soc. 1980, 102: 4438

<A NAME="RZ09304SS-7C">7c</A> Scaianó JC. Schmid P. Ingold KU. J. Organomet. Chem. 1976, 121: C4

<A NAME="RZ09304SS-8">8</A> Hu NX. Aso Y. Otsubo T. Ogura F. Bull. Chem. Soc. Jpn. 1986, 59: 879

<A NAME="RZ09304SS-9">9</A> Huang ZZ. Ye S. Xia W. Yu Y.-H. Tang Y. J. Org. Chem. 2002, 67: 3096

<A NAME="RZ09304SS-10">10</A> Miyashita M. Suzuki T. Hoshino M. Yoshikoshi A. Tetrahedron 1997, 53: 12469

<A NAME="RZ09304SS-11A">11a</A> Weller F. Adel J. Dehnicke K. Z. Anorg. Allg. Chem. 1987, 548: 125

<A NAME="RZ09304SS-11B">11b</A> Sheldrick WS. Braunbeck HG. Z. Naturforsch. B: Chem. Sci. 1989, 44: 1397

<A NAME="RZ09304SS-11C">11c</A> Fenske D. Kräuter G. Dehnicke K. Angew. Chem., Int. Ed. Engl. 1990, 4: 390

<A NAME="RZ09304SS-11D">11d</A> Müller V. Grebe C. Müller U. Dehnicke K. Z. Anorg. Allg. Chem. 1993, 619: 416

<A NAME="RZ09304SS-11E">11e</A> Müller V. Ahle A. Frenzen G. Neumüller B. Dehnicke K. Z. Anorg. Allg. Chem. 1993, 619: 1247

<A NAME="RZ09304SS-12">12</A> Farrall MJ. Fréchet JMJ. J. Org. Chem. 1976, 41: 3877