Synthesis of 7-substituted-5-androstene derivatives promoted by SmI 2

Steroids

Volumn 71, Issue 2, 2006, Pages 96-101

  Gu, Qin ^a   Zheng, Yun Hong ^a   Li, Yuan Chao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

, Unsaturated ketone; 7 Substituted 5 androstene derivatives; SmI2 mediated coupling reaction

Indexed keywords

3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7ALPHA (2 ETHOXY 2 OXOETHYL)ANDROST 5 EN 7BETA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7ALPHA ALLYANDROST 5 EN 7BETA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7ALPHA BENZYLADROST 5 EN 7BETA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7ALPHA BENZYLOXYMETHYLANDROST 5 EN 7BETA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7ALPHA METHYLANDROST 5 EN 7BETA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA (2 ETHOXY 2 OXOETHYL)ANDROST 5 EN 7ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA ALLYANDROST 5 EN 7ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA BENZYLADROST 5 EN 7ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA BENZYLOXYMETHYLANDROST 5 EN 7ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA BUTYLANDROST 5 EN 7 ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA ETHYLANDROST 5 EN 7 ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA ISOPRIOPYLANDROST 5 EN 7ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA ISOPRIOPYLANDROST 5 EN 7BETA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA METHYLANDROST 5 EN 7ALPHA OL; 3BETA,17BETA DI(TERT BUTYLDIMETHYLSILYLOXY)7BETA(6 CHLOROHEXYL)ANDROST 5 EN 7ALPHA OL; ANDROSTANE DERIVATIVE; HALIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ANDROSTENES; CARBON ISOTOPES; CHROMATOGRAPHY; IODIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; SAMARIUM; STEREOISOMERISM;

EID: 30644465043     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.08.008     Document Type: Article

References (10)

1. 2 and their use as reducing or coupling agents J Am Chem Soc 102 8 1980 2693 2698
2. 2, the Kagan reagent Chem Rev 99 3 1999 745 777
3. G.A. Molander Reductions with samarium(II) iodide L.A. Paquette Organic reactions vol. 46 1994 John Wiley & Sons Chichester 211 367
4. Y.-H. Zheng, and Y.-C. Li Novel stereoselective synthesis of 7β-methyl-substituted 5-androstene derivatives J Org Chem 68 4 2003 1603 1606
5. 2-THF solution in the presence of hexamethylphosphoric triamide (HMPA) Chem Lett 1987 1485 1486
6. T. Imamoto, T. Takeyama, and M. Yokoyama A new method for the hydroxymethylation of carbonyl compounds Tetrahedron Lett 25 30 1984 3225 3226
7. T. Imamoto, T. Hatajima, N. Takiyama, T. Takeyama, Y. Kamiya, and T. Yoshizawa Reactions of carbonyl compounds with benzyl chloromethyl ether of diiodomethane in the presence of samarium(II) iodide or metallic samarium. New routes to 1,2-diols, iodohydrins and cyclopropanols J Chem Soc, Perkin Trans I 1991 3127 3135
8. F. Machrouhi, B. Hamann, J.L. Namy, and H.B. Kagan Improved reactivity of diiodosamarium by catalysis with transition metal salts Synlett 1996 633 634
9. K. Utimoto, and S. Matsubara Samarium diiodide-mediated reaction of organic halides with carbonyl compounds J Synth Org Chem Jpn 56 11 1998 908 918
10. H. Eggert, C.L. vanAntwerp, N.S. Bhacca, and C. Djerassi Carbon-13 nuclear magnetic resonance spectra of hydroxyl steroids J Org Chem 41 1 1976 71 78