Polyhydroxylated pyrrolizidines. Part 6: A new and concise stereoselective synthesis of (+)-casuarine and its 6,7-diepi isomer, from DMDP

Tetrahedron

Volumn 61, Issue 27, 2005, Pages 6527-6533

  Izquierdo, Isidoro ^a   Plaza, María T ^a   Tamayo, Juan A ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

(+) Casuarine; 6,7 Diepicasuarine; DMDP; Polyhydroxylated pyrrolizidines; Stereoselective synthesis

Indexed keywords

3,4 DIBENZYLOXY 2' O TERT BUTYLDIPHENYLSILYL 2,5 BIS(HYDROXYMETHYL) PYRROLIDINE; 6,7 DIEPICASUARINE; CASUARINE; PYRROLIZIDINE ALKALOID; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 20444438808     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.004     Document Type: Article

References (19)

1. I. Izquierdo, M.-T. Plaza, and J.A. Tamayo Tetrahedron: Asymmetry 15 2004 3635
2. N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1645
3. P. Compain, and O.R. Martin Bioorg. Med. Chem. 9 2001 3077
4. A.A. Watson, G.W.J. Fleet, N. Asano, R.J. Molyneux, and R.J. Nash Phytochemistry 56 2001 265
5. N. Asano Glycobiology 13 2003 93R
6. T. Ayad, Y. Genisson, and M. Baltas Curr. Org. Chem. 8 2004 1211
7. I. Izquierdo, M.-T. Plaza, and F. Franco Tetrahedron: Asymmetry 13 2002 1581
8. I. Izquierdo, M.-T. Plaza, and F. Franco Tetrahedron: Asymmetry 14 2003 3933
9. I. Izquierdo, M.-T. Plaza, and F. Franco Tetrahedron: Asymmetry 15 2004 1465
10. A. Kato, I. Adachi, M. Miyauchi, K. Ikeda, T. Komae, H. Kizu, Y. Kameda, A.A. Watson, R.J. Nash, M.R. Wormald, G.W.J. Fleet, and N. Asano Carbohydr. Res. 316 1999 95
11. R.J. Nash, P.I. Thomas, R.D. Waigh, G.W.J. Fleet, M.R. Wormald, P. M. de Q. Lilley, and D.J. Watkin Tetrahedron Lett. 35 1994 7849
12. I. Izquierdo, M.-T. Plaza, and F. Franco Tetrahedron: Asymmetry 13 2002 1503
13. S.E. Denmark, and A.R. Hurd Org. Lett. 1 1999 1311
14. S.E. Denmark, and A.R. Hurd J. Org. Chem. 65 2000 2875
15. A.A. Bell, L. Pickering, A.A. Watson, R.J. Nash, Y.T. Pan, A.D. Elbein, and G.W.J. Fleet Tetrahedron Lett. 38 1997 5869
16. 13C NMR spectra indicates that rotamers are present.
17. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483
18. E.N. Jacobsen, I. Markó, S.W. Mungall, G. Schröder, and K.B. Sharpless J. Am. Chem. Soc. 110 1998 1968
19. K.B. Sharpless, W. Amberg, Y.L. Bennani, G.A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, and X.-L. Zhang J. Org. Chem. 57 1992 2768