A stereoselective approach to polyhydroxylated quinolizidine alkaloids

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8537-8540

  Carretero, Juan C ^a   Arrayás, Ramón Gómez ^a   Storch De Gracia, Isabel ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLIZIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0342940774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10241-6     Document Type: Article

References (29)

1. For a recent review, see: Robins, D. J. Nat. Prod. Rep. 1995, 12, 413.
2. For a recent review, see: Michael, J. P. Nat. Prod. Rep. 1995, 12, 535.
3. For a review, see: Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W.; Ed. Wiley: New York, 1987; Vol. 5, Chapter 1.
4. For a review on synthesis of castanopermine and analogues, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045. For some recent references, see: Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547.
5. For a review on synthesis of castanopermine and analogues, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045. For some recent references, see: Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547.
6. b) Mootoo, D. R.; Zhao, H. J. Org. Chem. 1996, 61, 6762.
7. c) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7219.
8. a) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5537.
9. b) Herczegh, P.; Kovács, I.; Szilágyi, I.; Sztaricskai, F.; Berecibar, A.; Riche, C.; Chironi, A.; Olesker, A.; Lukacs, G. Tetrahedron 1995, 51, 2969.
10. c) Gradnig, G.; Berger, A.; Grassberger, V.; Stütz, A. E.; Legler, G. Tetrahedron Lett. 1991, 32, 4889.
11. d) Liu, P. S.; Rogers, R. S.; Kang, M. S.; Sunkara, P. S. Tetrahedron Lett. 1991, 32, 5853.
12. e) Hamana, H.; Ikota, N.; Ganern, B. J. Org. Chem. 1987, 52, 5492.
13. For the synthesis of racemic and enantiomerically pure γ-hydroxy-α,β-unsaturated phenyl sulfones see: a) Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.
14. b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 5159.
15. c) Dominguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197
16. a) Synthesis of [3.3.0] and [4.3.0] bicyclic compounds: Adrio, J.; Carretero, J. C.; Gómez Arrayás, R. Synlett 1996, 640.
17. b) Synthesis of indolizidines: Carretero, J. C.; Gómez Arrayás, R. J. Org. Chem. 1995, 60, 6000.
18. c) Synthesis of polypropionate chains: Carretero, J. C.; Dominguez, E. J. Org. Chem. 1993, 58, 1596.
19. Carretero, J. C.; Gómez Arrayás, R.; Storch de Gracia, I. Tetrahedron Lett. 1996, 37, 3379.
20. It is interesting to note that although in this cyclic β-hydroxysulfone the OH group is in equatorial position, its reaction with Na(Hg) occurred with formation of the C-C double bond (Julia olefination) instead of the reductive elimination of the sulfone. So, it is not required its previous activation as acetate or mesylate derivative. For the Julia olefination in cycles, see: Kocienski, P. J. Chem. Ind. (London) 1981, 548.
21. 1H-NMR, mainly by analysis of their vecinal coupling constants (see figures below). (figure presented)
22. 2) a complex mixture of products was obtained.
23. The opposite stereoselectivity observed in the epoxidation of 6 (compared with its dihydroxylation) could be due to the association of the peracid with the ammonium salt, likely by hydrogen bonding, which would direct the approach of the peracid from the lower face of the olefin (see figure). (figure presented)
24. Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515.
25. In this case a minor amount of the trans-diequatorial product was also formed (15% yield).
26. For direct dialkylations of β-nitrogenated sulfones to form six member rings, see: a) Alonso, D. A.; Costa, A.; Mancheño, B.; Nájera, C. Tetrahedron 1997, 53, 4791.
27. b) Caturla, F.; Nájera, C. Tetrahedron Lett. 1997, 38, 3789.
28. 2) the desired ketone 15 was obtained in very low yields.
29. 9a (70:30 ratio of isomers).