Totally Stereocontrolled Nitrone-Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N.-Boc-phenylisoserine

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6672-6677

  Jost, Sylvie ^a   Gimbert, Yves ^a   Greene, Andrew E ^a   Fotiadu, Frédéric ^b  

^a UNIV GRENOBLE ALPES   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; BACCATIN III; DOCETAXEL; ISOSERINE; ISOXAZOLIDINE DERIVATIVE; KETENE DERIVATIVE; NITRO DERIVATIVE; PACLITAXEL;

ARTICLE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; RACEMIC MIXTURE; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030820055     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971009v     Document Type: Article

References (53)

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33. Kita, Y.; Tamura, O.; Itoh, F.; Kishino, H.; Miki, T.; Kohno, M.; Tamura, Y. J. Chem. Soc., Chem. Commun. 1988, 761.
34. For examples of the application of chiral nitrones and chiral dipolarophiles in asymmetric synthesis, see: Murahashi, S.-I.; Imada, Y.; Kohno, M; Kawakami, T. Synlett 1993, 395. For an alternative approach, see: Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419.
35. For examples of the application of chiral nitrones and chiral dipolarophiles in asymmetric synthesis, see: Murahashi, S.-I.; Imada, Y.; Kohno, M; Kawakami, T. Synlett 1993, 395. For an alternative approach, see: Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419.
36. Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymmetry 1995, 6, 1441.
37. Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron 1985, 41, 3455.
38. Ketene acetal 3 was prepared by a modification of the procedure described by Hattori and Yamamoto: Hattori, K.; Yamamoto, H. J. Org. Chem. 1993, 58, 5301. The E:Z ratio was 74:26. The tertbutyldimethylsilyl and benzyl protecting groups were found to be less effective in this work.
39. These ratios were determined by proton NMR analysis. The anti-syn stereochemical assignments were established by NMR after cyclization of the purified or partially purified components to the corresponding isoxazolidinones; the absolute stereochemistry was assigned after conversion of the isoxazolidinones to the known isoserine derivatives.
40. The corresponding Z ketene acetal produced a 63:37 anti to syn ratio in 63% yield.
41. 12 to the corresponding hydroxylamine, which was condensed with benzaldehyde to give the nitrone. Disappointingly, although the ratio of the anti diastereomers improved (89:11) while the combined yield remained high (92%), the anti and syn products were now formed in similar amounts (56:44).
42. 12 to the corresponding hydroxylamine, which was condensed with benzaldehyde to give the nitrone. Disappointingly, although the ratio of the anti diastereomers improved (89:11) while the combined yield remained high (92%), the anti and syn products were now formed in similar amounts (56:44).
43. 12 to the corresponding hydroxylamine, which was condensed with benzaldehyde to give the nitrone. Disappointingly, although the ratio of the anti diastereomers improved (89:11) while the combined yield remained high (92%), the anti and syn products were now formed in similar amounts (56:44).
44. 12 to the corresponding hydroxylamine, which was condensed with benzaldehyde to give the nitrone. Disappointingly, although the ratio of the anti diastereomers improved (89:11) while the combined yield remained high (92%), the anti and syn products were now formed in similar amounts (56:44).
45. Whitesell, J. K.; Lawrence, R. M. Chim. 1986, 40, 318. The other chiral auxiliaries examined were 8-phenylmenthol, phenylethanol, and 3,3-dimethyl-2-butanol.
46. Georg. G. I.; Cheruvallath, Z. S.; Himes, R. H.; Mejillano, M. R.; Burke, C. T. J. Med. Chem. 1992, 35, 4230.
47. Murahasi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736. Murahashi, S.-I.; Shiota, T.; Imada, Y. Org. Synth. 1991, 70, 265.
48. Murahasi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736. Murahashi, S.-I.; Shiota, T.; Imada, Y. Org. Synth. 1991, 70, 265.
49. See: Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
50. In this preliminary study the AM1 semiempirical molecular orbital method was employed (Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902). All calculations were performed with the AMPAC 4.5 code (Semichem, Shawnes, KS 66216).
51. The RHF, closed-shell, ground state was used in all cases. Force calculations were performed on the local minima and the transition states to verify that they had no and one and only one negative force constant, respectively. In addition, some ab initio calculations have been carried out with the 3-21G* basis set using the Gaussian 92 program on stationary points found at the semiemprical level (Frisch, M. J.; Trucks, G. W.; Head-Gordon, M,; Gill, W. P. M.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Reploge, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92; Gausssian Inc.: Pittsburgh, PA, 1992). Details can be found in the Supporting Information.
52. For the analytical instruments used in this work, see: B. M. de Azevedo, M.; Greene, A. E. J. Org. Chem. 1995, 60, 4940.
53. Davis, F. A.; Reddy, R. T.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387.