Synthesis of Novel Structurally
Simplified Estrogen Analogues with Electron-Donating Groups in Ring
A

Lutz F. Tietze; Carsten A. Vock; Ilga K. Krimmelbein; Linda Nacke

doi:10.1055/s-0029-1216810

PAPER

Synthesis of Novel Structurally Simplified Estrogen Analogues with Electron-Donating Groups in Ring A

Lutz F. Tietze*, Carsten A. Vock, Ilga K. Krimmelbein, Linda Nacke
Institute of Organic and Biomolecular Chemistry, University of Goettingen, Tammannstr. 2, 37077 Goettingen, Germany
Fax: +49(551)399476; e-Mail: ltietze@gwdg.de;

Abstract

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Abstract

A library of 25 novel estrogen analogues were prepared in five to eight steps from mostly commercially available substituted anisoles via bromination, formylation, Corey-Fuchs reaction, elimination, and Sonogashira reaction.

Key words

alkynes - estrogens - Corey-Fuchs reaction - Sonogashira reaction - steroids

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References

<A NAME="RT20108SS-1">1</A> Tietze LF. Vock CA. Krimmelbein IK. Wiegand JM. Nacke L. Ramachandar T. Islam KMD. Gatz C. Chem. Eur. J. 2008, 14: 3670

<A NAME="RT20108SS-2">2</A> Islam KMD. Dilcher M. Thurow C. Vock C. Krimmelbein I. Tietze LF. Gonzalez V. Zhao H. Gatz C. Protein Eng. Des. Sel. 2009, 22: 45

Examples:

<A NAME="RT20108SS-3A">3a</A> Myers MJ. Sun J. Carlson KE. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem. 1999, 42: 2456

<A NAME="RT20108SS-3B">3b</A> Myers MJ. Sun J. Carlson KE. Marriner GA. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem. 2001, 44: 4230

<A NAME="RT20108SS-3C">3c</A> Stauffer SR. Coletta CJ. Tedesco R. Nishiguchi G. Carlson K. Sun J. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem. 2000, 43: 4934

<A NAME="RT20108SS-3D">3d</A> Mortensen DS. Rodriguez AL. Carlson KE. Sun J. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem. 2001, 44: 3838

<A NAME="RT20108SS-3E">3e</A> Muthyala RS. Sheng S. Carlson KE. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem. 2003, 46: 1589

<A NAME="RT20108SS-3F">3f</A> Dowers TS. Qin Z. Thatcher GRJ. Bolton JL. Chem. Res. Toxikol. 2006, 19: 1125

<A NAME="RT20108SS-3G">3g</A> Zhao L. Jin C. Mao Z. Gopinathan MB. Rehder K. Brinton RD. J. Med. Chem. 2007, 50: 4471

<A NAME="RT20108SS-4">4</A> Silberberg SD. Magleby KL. Science 1999, 285: 1859

<A NAME="RT20108SS-5">5</A> Mendelsohn ME. Karas RH. N. Engl. J. Med. 1999, 340: 1801

Examples:

<A NAME="RT20108SS-6A">6a</A> Funk RL. Vollhardt KPC. J. Am. Chem. Soc. 1979, 101: 215

<A NAME="RT20108SS-6B">6b</A> Funk RL. Vollhardt KPC. J. Am. Chem. Soc. 1980, 102: 5253

<A NAME="RT20108SS-6C">6c</A> Oppolzer W. Bättig K. Petrzilka M. Helv. Chim. Acta 1978, 61: 1945

<A NAME="RT20108SS-6D">6d</A> Oppolzer W. Roberts DA. Bird TGC. Helv. Chim. Acta 1979, 62: 2017

<A NAME="RT20108SS-6E">6e</A> Nicolaou KC. Barnette WE. Ma P. J. Org. Chem. 1980, 45: 1463

<A NAME="RT20108SS-6F">6f</A> Posner GH. Hulce H. Tetrahedron Lett. 1984, 25: 379

<A NAME="RT20108SS-6G">6g</A> Charlton JL. Alauddin MM. Tetrahedron 1987, 43: 2873

<A NAME="RT20108SS-6H">6h</A> Doi T. Shimizu K. Takahashi T. Tsuji J. Yamamoto K. Tetrahedron Lett. 1990, 31: 3313

<A NAME="RT20108SS-6I">6i</A> Kametani T. Pure Appl. Chem. 1979, 51: 747

<A NAME="RT20108SS-6J">6j</A> Kametani T. Nemoto H. Tetrahedron 1981, 37: 3

<A NAME="RT20108SS-6K">6k</A> Groth U. Richter N. Kalogerakis A. Synlett 2006, 905

<A NAME="RT20108SS-6L">6l</A> Groth U. Koehler T. Taapken T. Tetrahedron 1991, 47: 7583

<A NAME="RT20108SS-7A">7a</A> Tietze LF. Nöbel T. Spescha M. Angew. Chem., Int. Ed. Engl. 1996, 35: 2259 ; Angew. Chem. 1996, 108, 2385

<A NAME="RT20108SS-7B">7b</A> Tietze LF. Nöbel T. Spescha M. J. Am. Chem. Soc. 1998, 120: 8971

<A NAME="RT20108SS-8A">8a</A> Tietze LF. Petersen S. Eur. J. Org. Chem. 2000, 1827

<A NAME="RT20108SS-8B">8b</A> Tietze LF. Petersen S. Eur. J. Org. Chem. 2001, 1619

<A NAME="RT20108SS-8C">8c</A> Tietze LF. Wiegand JM. Vock CA. J. Organomet. Chem. 2003, 687: 346

<A NAME="RT20108SS-8D">8d</A> Tietze LF. Wiegand JM. Vock CA. Eur. J. Org. Chem. 2004, 4107

<A NAME="RT20108SS-8E">8e</A> Tietze LF. Schneider G. Wölfling J. Fecher A. Nöbel T. Petersen S. Schuberth I. Wulff C. Chem. Eur. J. 2000, 6: 3755

<A NAME="RT20108SS-9">9</A> Tietze LF. Krimmelbein IK. Chem. Eur. J. 2008, 14: 1541

<A NAME="RT20108SS-10">10</A> Shieh W.-C. Dell S. Repič O. Org. Lett. 2001, 3: 4279

<A NAME="RT20108SS-11">11</A> Andersh B. Murphy DL. Olson RJ. Synth. Commun. 2000, 30: 2091

<A NAME="RT20108SS-12">12</A> Karl J. Gust R. Spruss T. Schneider MR. Schoenenberg H. J. Med. Chem. 1988, 31: 72

<A NAME="RT20108SS-13">13</A> Corey EJ. Fuchs PL. Tetrahedron Lett. 1972, 3769

<A NAME="RT20108SS-14A">14a</A> Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 4467

<A NAME="RT20108SS-14B">14b</A> Takahashi S. Kuroyama Y. Sonogashira K. Hagihara N. Synthesis 1980, 627

<A NAME="RT20108SS-14C">14c</A> Sonogashira K. In Comprehensive Organic Synthesis Vol. 3: Trost BM. Fleming I. Pattenden G. Pergamon; Oxford: 1991.

<A NAME="RT20108SS-15">15</A> Tamura R. Kohno M. Utsunomiya S. Yamawaki K. Azuma N. Matsumoto A. Ishii Y. J. Org. Chem. 1993, 58: 3953

<A NAME="RT20108SS-16">16</A> Kemperman GJ. Roeters TA. Hilberink PW. Eur. J. Org. Chem. 2003, 1681

<A NAME="RT20108SS-17">17</A> Piers E. Grierson JR. Lau CK. Nagakura I. Can. J. Chem. 1982, 60: 210