Grignard reagent induced tandem semipinacol rearrangement/ketone addition reaction of 20S-hydroxy-5α-pregnane-16(17)-epoxide

Tetrahedron Letters

Volumn 52, Issue 32, 2011, Pages 4123-4125

  Huang, Chun Xi ^a   Shi, Yong ^b   Lin, Jing Rong ^a   Jin, Rong Hua ^a   Tian, Wei Sheng ^b  

^a SHANGHAI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Epoxide opening; Grignard reagent; Semipinacol rearrangement; Tandem reaction

Indexed keywords

EPOXIDE; HYDROXY 5A PREGNANE 16(17)EPOXIDE; KETONE; MAGNESIUM OXIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; GRIGNARD REACTION; STEREOCHEMISTRY; TANDEM SEMIPINACOL REARRANGEMENT;

EID: 79960390181     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.122     Document Type: Article

References (16)

1. D.J. Coveney B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 3 1991 Pergamon Oxford p 777
2. T.J. Snape Chem. Soc. Rev. 36 2007 1823 1842
3. M.E. Jung, and A. van den Heuvel Org. Lett. 5 2003 4705 4707
4. C.-A. Fan, B.-M. Wang, Y.-Q. Tu, and Z.-L. Song Angew. Chem., Int. Ed. 40 2001 3877 3880
5. Y.Q. Tu, L.D. Sun, and P.Z. Wang J. Org. Chem. 64 1990 629 633
6. X.-D. Hu, C.-A. Fan, F.-M. Zhang, and Y.Q. Tu Angew. Chem., Int. Ed. 43 2004 1702 1705
7. C.-A. Fan, X.-D. Hu, Y.-Q. Tu, B.-M. Wang, and Z.-L. Song Chem. Eur. J. 9 2003 4301 4310
8. A. Plaza, A. Perrone, M.L. Balestrieri, F. Felice, C. Balestrieri, A.I. Hamed, C. Pizza, and S. Piacente Steroids 70 2005 594 603
9. M. Cabeza, E. Gutiérrez, R. Miranda, I. Heuze, E. Bratoeff, G. Flores, and E. Ramírez Steroids 64 1999 413 421
10. N. Kongkathip, B. Kongkathip, and N. Noimai Synth. Commun. 36 2006 865 874
11. E.L. Shapiro, M. Steinberg, D. Gould, M.J. Gentles, H.L. Herzog, M. Gilmore, W. Charney, E.B. Hershberg, and L. Mandell J. Am. Chem. Soc. 81 1959 6483 6486
12. A.R. Angeles, S.P. Waters, and S.J. Danishefsky J. Am. Chem. Soc. 130 2008 13765 13770
13. M.E. Jung, and D.C. D'Amico J. Am. Chem. Soc. 115 1993 12208 12209
14. M.E. Jung, W.S. Lee, and D. Sun Org. Lett. 1 1999 307 310
15. M.E. Jung, and A. van den Heuvel Tetrahedron Lett. 43 2002 8169 8172
16. Z.-J. Zheng, X.-Z. Shu, K.-G. Ji, S.-C. Zhao, and Y.-M. Liang Org. Lett. 11 2009 3214 3217