Asymmetric synthesis of (-)-(1R,7aS)-absouline

Tetrahedron

Volumn 69, Issue 4, 2013, Pages 1369-1377

  Davies, Stephen G ^a   Fletcher, Ai M ^a   Lebée, Clément ^a   Roberts, Paul M ^a   Thomson, James E ^a   Yin, Jingda ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

( ) (1R,7aS) Absouline; Asymmetric synthesis; Conjugate addition; Lithium amide

Indexed keywords

1 AMINOPYRROLIZIDIN 3 ONE; 4 METHOXYCINNAMIC ACID; ABSOULINE; CINNAMIC ACID DERIVATIVE; ESTER DERIVATIVE; LITHIUM N BENZYL N (ALPHA METHYLBENZYL)AMIDE; PROLINE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CYCLIZATION; HYDROGENOLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 84871972980     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.080     Document Type: Article

References (30)

1. A.A. Watson, G.W.J. Fleet, N. Asano, R.J. Molyneux, and R.J. Nash Phytochemistry 56 2001 265
2. D.P. Becker, D.L. Flynn, and C.I. Villamil Bioorg. Med. Chem. Lett. 14 2004 3073
3. N. Asano, H. Kuroi, K. Ikeda, H. Kizu, Y. Kameda, A. Kato, I. Adachi, A.A. Watson, R.J. Nash, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1
4. M. Shibano, D. Tsukamoto, and G. Kusano Chem. Pharm. Bull. 47 1999 907
5. K. Ikhiri, A. Ahond, C. Poupat, P. Potier, J. Pusset, and T. Sévenet J. Nat. Prod. 50 1987 626
6. C. Christine, K. Ikhiri, A. Ahond, A. Al Mourabit, C. Poupat, and P. Potier Tetrahedron 56 2000 1837
7. K. Muñiz, J. Streuff, P. Chávez, and C.H. Hövelmann Chem. Asian J. 3 2008 1248
8. T. Tang, Y.-P. Ruan, J.-L. Ye, and P.-Q. Huang Synlett 2005 231
9. M. Vargas-Sanchez, F. Couty, G. Evano, D. Prim, and J. Marrot Org. Lett. 7 2005 5861
10. E.J. Eklund, R.D. Pike, and J.R. Scheerer Tetrahedron Lett. 53 2012 4644
11. T. Tang, C. Zhu, and P.-Q. Huang Heterocycles 64 2004 121
12. S.G. Davies, J.A. Lee, P.M. Roberts, J.E. Thomson, and J. Yin Org. Lett. 14 2012 218
13. S.G. Davies, D. Díez, M.M. El Hammouni, A.C. Garner, N.M. Garrido, M.J.C. Long, R.M. Morrison, A.D. Smith, M.J. Sweet, and J.M. Withey Chem. Commun. 2003 2410
14. S.G. Davies, A.C. Garner, M.J.C. Long, A.D. Smith, M.J. Sweet, and J.M. Withey Org. Biomol. Chem. 2 2004 3355
15. S.G. Davies, A.C. Garner, M.J.C. Long, R.M. Morrison, P.M. Roberts, E.D. Savory, A.D. Smith, M.J. Sweet, and J.M. Withey Org. Biomol. Chem. 3 2005 2762
16. Y. Aye, S.G. Davies, A.C. Garner, P.M. Roberts, A.D. Smith, and J.E. Thomson Org. Biomol. Chem. 6 2008 2195
17. E. Abraham, S.G. Davies, A.J. Docherty, K.B. Ling, P.M. Roberts, A.J. Russell, J.E. Thomson, and S.M. Toms Tetrahedron: Asymmetry 19 2008 1356
18. S.G. Davies, M.J. Durbin, S.J.S. Hartman, A. Matsuno, P.M. Roberts, A.J. Russell, A.D. Smith, J.E. Thomson, and S.M. Toms Tetrahedron: Asymmetry 19 2008 2870
19. A. Horeau Tetrahedron 31 1975 1307
20. J.F. Costello, S.G. Davies, and O. Ichihara Tetrahedron: Asymmetry 5 1994 1999
21. N. Giri, M. Petrini, and R. Profeta J. Org. Chem. 69 2004 7303
22. S.G. Davies, A.D. Smith, and P.D. Price Tetrahedron: Asymmetry 16 2005 2833
23. S.G. Davies, A.M. Fletcher, P.M. Roberts, and J.E. Thomson Tetrahedron: Asymmetry 23 2012 1111
24. S.G. Davies, M.J. Durbin, E.C. Goddard, P.M. Kelly, W. Kurosawa, J.A. Lee, R.L. Nicholson, P.M. Price, P.M. Roberts, A.J. Russell, P.M. Scott, and A.D. Smith Org. Biomol. Chem. 7 2009 761
25. S.G. Davies, J.A. Lee, P.M. Roberts, J.E. Thomson, and J. Yin Tetrahedron 67 2011 6382
26. S.G. Davies, A.M. Fletcher, G.J. Hermann, G. Poce, P.M. Roberts, A.D. Smith, M.J. Sweet, and J.E. Thomson Tetrahedron: Asymmetry 21 2010 1635
27. S.G. Davies, R.L. Nicholson, P.D. Price, P.M. Roberts, A.J. Russell, E.D. Savory, A.D. Smith, and J.E. Thomson Tetrahedron: Asymmetry 20 2009 758
28. S.G. Davies, E.M. Foster, A.B. Frost, J.A. Lee, P.M. Roberts, and J.E. Thomson Org. Biomol. Chem. 10 2012 6186
29. A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Timmers Organometallics 15 1996 1518
30. C.J. Deur, M.W. Miller, and L.S. Hegedus J. Org. Chem. 61 1996 2871