Synthetic Approaches towards 4-Functionalized Estrone Derivatives

Uwe Schön; Josef Messinger; Wladimir Solodenko; Andreas Kirschning

doi:10.1055/s-0032-1316816

Synthesis, Table of Contents

Synthesis 2012; 44(24): 3822-3828
DOI: 10.1055/s-0032-1316816

paper

Synthetic Approaches towards 4-Functionalized Estrone Derivatives

Authors

Uwe Schön

^aAbbott Products GmbH, Abbott Laboratories GmbH, Freundallee 9A, 30173 Hannover, Germany
Josef Messinger

^aAbbott Products GmbH, Abbott Laboratories GmbH, Freundallee 9A, 30173 Hannover, Germany
Wladimir Solodenko

^bInstitut für Organische Chemie and Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany Email: andreas.kirschning@oci.uni-hannover.de
Andreas Kirschning*

^bInstitut für Organische Chemie and Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany Email: andreas.kirschning@oci.uni-hannover.de

Abstract

All articles of this category

Abstract

Directed ortho-lithiation of estrone carbamate followed by reaction with electrophiles afforded 2-substituted estrone derivatives. Reductive cleavage of the carbamate group followed by O-allylation and Claisen rearrangement led to new 4-functionalized estrone derivatives.

Key words

carbanions - Claisen rearrangement - estrone - ortho-lithiation - steroids

Full Text

References

References
1 Dence JB. Steroids and Peptides . Wiley-Interscience; New York: 1980
2 Johns WF. MTP International Review of Science . Vol. 8. Chemistry Park Press; Baltimore: 1973

3a Turner AB. Nat. Prod. Rep. 1992; 9: 37
3b Turner AB. Nat. Prod. Rep. 1989; 6: 539
3c Trost BM, Kulawiec RJ, Mammes A. Tetrahedron Lett. 1993; 34: 587

4 Wilson SR, Yasmin A In Studies in Natural Products Chemistry . Vol. 10. Atta-ur-Rahman Elsevier; Amsterdam: 1992: 43-75

5a Radpath J, Zeelen FJ. Chem. Soc. Rev. 1983; 12: 75
5b Kametani T. Actual. Chim. Theor. 1988; 15: 131

6 Broach JR, Thorner J. Nature 1996; 384: 14
7 Messinger J, Husen B, Koskimies P, Hirvela L, Kallio L, Saarenketo P, Thole H. Mol. Cell. Endocrinol. 2009; 301: 216
8 Maltais R, Tremblay MR, Ciobanu LC, Poirier D. J. Comb. Chem. 2004; 6: 443

9a Troisi L, Vasapollo G, El Ali B, Mele G, Florio S, Capriati V. Tetrahedron Lett. 1999; 40: 1771
9b Holton PG. J. Org. Chem. 1962; 27: 357
9c Patton TL. J. Org. Chem. 1962; 27: 910
9d Barner R, Boller A, Borgulya J, Herzog EG, von Philipsborn W, von Planta C, Fürst A, Schmid H. Helv. Chim. Acta 1965; 48: 94

10a Snieckus V. Chem. Rev. 1990; 90: 879
10b Hartung CG, Snieckus V In Modern Arene Chemistry . Astruc D. Wiley-VCH; Weinheim: 2002: 330-367

11a Pert DJ, Ridley DD. Aust. J. Chem. 1987; 40: 303
11b Leese MP, Newman SP, Purohit A, Reed MJ, Potter BV. L. Bioorg. Med. Chem. Lett. 2004; 14: 3135

12 Sibi MP, Snieckus V. J. Org. Chem. 1983; 48: 1935
13 Austin WF, Zhang Y, Danheiser RL. Tetrahedron 2008; 65: 915
14 Szele I. Helv. Chim. Acta 1981; 64: 2733
15 Rao PN, Wang Z. Steroids 1997; 64: 487
16 Smith A. US Patent 3138588, 1964
17 Danishefsky S, Cain P. J. Am. Chem. Soc. 1975; 97: 5282
18 Quinkert G, Del Grosso M, Döring A, Döring W, Schenkel RI, Bauch M, Dambacher GT, Bats JW, Zimmermann G, Dürner G. Helv. Chim. Acta 1995; 78: 1345