A versatile approach to N-Boc-statine and N-Boc-norstatine based on the reduction of 1-trialkylsilyl acetylenic ketones. Strong remote effect of the C(1) substituent on the stereoselectivity

Organic Letters

Volumn 1, Issue 11, 1999, Pages 1831-1834

  Alemany, Carme ^a   Bach, Jordi ^a   Farràs, Jaume ^a   Garcia, Jordi ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000106284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991098t     Document Type: Article

References (30)

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4. Hossain, H. B.; van der Helm, D.; Antel, J.; Sheldrick, G. M.; Sanduja, S. K.; Weinheimer, A. J. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4118; Banaigs, B.; Jeanty, G.; Francisco, C.; Jouin, P.; Poncet, J.; Heitz, A.; Cave, A.; Prome, J. C.; Wahl, M.; Lafargue, F. Tetrahedron 1989, 45, 181. For nordidemnin B, a closely related natural product, see: Jouin, P.; Poncet, J.; Dufbur, M.; Pantaloni, A.; Castro, B. J. Org. Chem. 1989, 54, 617.
5. Hossain, H. B.; van der Helm, D.; Antel, J.; Sheldrick, G. M.; Sanduja, S. K.; Weinheimer, A. J. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4118; Banaigs, B.; Jeanty, G.; Francisco, C.; Jouin, P.; Poncet, J.; Heitz, A.; Cave, A.; Prome, J. C.; Wahl, M.; Lafargue, F. Tetrahedron 1989, 45, 181. For nordidemnin B, a closely related natural product, see: Jouin, P.; Poncet, J.; Dufbur, M.; Pantaloni, A.; Castro, B. J. Org. Chem. 1989, 54, 617.
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11. For a review on syntheses of β-amino acids, see: Cole, D. C. Tetrahedron 1994, 50, 9517. For a discussion of the synthetic approaches to β-hydroxy γ-amino acids, see: Castejón, P.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 7063. See also: Pastó, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1996, 7, 243.
12. For a review on syntheses of β-amino acids, see: Cole, D. C. Tetrahedron 1994, 50, 9517. For a discussion of the synthetic approaches to β-hydroxy γ-amino acids, see: Castejón, P.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 7063. See also: Pastó, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1996, 7, 243.
13. For a review on syntheses of β-amino acids, see: Cole, D. C. Tetrahedron 1994, 50, 9517. For a discussion of the synthetic approaches to β-hydroxy γ-amino acids, see: Castejón, P.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 7063. See also: Pastó, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1996, 7, 243.
14. For example, see: Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301. See also: Jost, S.; Gimbert, Y.; Greene, A. E.; Fotiadu, F. J. J. Org. Chem. 1997, 62, 6672.
15. For example, see: Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301. See also: Jost, S.; Gimbert, Y.; Greene, A. E.; Fotiadu, F. J. J. Org. Chem. 1997, 62, 6672.
16. For example, see: Harris, B. C.; Joullié, M. M. Tetrahedron 1988, 44, 3489. Good results have been also reported with bulky N,N-dibenzyl-protected compunds, but the deprotection step was troublesome: Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. Chem. Commun. 1989, 1474. See also: Hoffman, R. V.; Tao, J. J. Org. Chem. 1997, 62, 2292 and references therein.
17. For example, see: Harris, B. C.; Joullié, M. M. Tetrahedron 1988, 44, 3489. Good results have been also reported with bulky N,N-dibenzyl-protected compunds, but the deprotection step was troublesome: Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. Chem. Commun. 1989, 1474. See also: Hoffman, R. V.; Tao, J. J. Org. Chem. 1997, 62, 2292 and references therein.
18. For example, see: Harris, B. C.; Joullié, M. M. Tetrahedron 1988, 44, 3489. Good results have been also reported with bulky N,N-dibenzyl-protected compunds, but the deprotection step was troublesome: Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. Chem. Commun. 1989, 1474. See also: Hoffman, R. V.; Tao, J. J. Org. Chem. 1997, 62, 2292 and references therein.
19. For a review on the synthesis of diastereomeric amino alcohols, see: Tramontini, M. Synthesis 1982, 605. See also ref 9.
20. Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021. Bach, J.; Garcia, J. Tetrahedron Lett. 1998, 39, 6761. Bach, J.; Galobardes, M.; Garcia, J.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 6765.
21. Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021. Bach, J.; Garcia, J. Tetrahedron Lett. 1998, 39, 6761. Bach, J.; Galobardes, M.; Garcia, J.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 6765.
22. Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021. Bach, J.; Garcia, J. Tetrahedron Lett. 1998, 39, 6761. Bach, J.; Galobardes, M.; Garcia, J.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 6765.
23. Compound 6c was obtained in only 30% yield.
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25. For a review on oxazaborolidine-mediated reductions, see: Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986. Remote repulsive interactions with the B-alkyl group in the reduction of α,β-ynones have been reported: Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
26. For a review on oxazaborolidine-mediated reductions, see: Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986. Remote repulsive interactions with the B-alkyl group in the reduction of α,β-ynones have been reported: Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
27. All ab initio calculations were carried out using the GAUSSIAN-94 (rev. E.1) series of programs (Gaussian, Inc., Pittsburgh, PA, 1995).
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29. Samples of stereochemically pure alcohols 10 were available by deprotection (aqueous MeOH, catalytic p-TsOH, rt) of pure oxazolidines 14.
30. Carlsen, H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.