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Volumn 65, Issue 18, 2000, Pages 5575-5589

Stereodivergent approaches to the synthesis of isoxazolidine analogoues of α-amino acid nucleosides. Total synthesis of isoxazolidinyl deoxypolyoxin C and uracil polyoxin C

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALPHA AMINO ACID; CARBON; DEOXYPOLYOXIN C; GLYCINE; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; KETENE DERIVATIVE; NITROGEN; NITROGEN DERIVATIVE; NITRONE DERIVATIVE; NUCLEOSIDE; POLYOXIN C; SERINE; UNCLASSIFIED DRUG;

EID: 0033824386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0002689     Document Type: Article
Times cited : (90)

References (129)
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    • We have amply demonstrated that nucleophilic additions to nitrones derived from serine can be stereocontrolled by the appropriate choice of the protecting groups in the nitrone. See: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 5627-5630. (b) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646. (c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
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    • We have amply demonstrated that nucleophilic additions to nitrones derived from serine can be stereocontrolled by the appropriate choice of the protecting groups in the nitrone. See: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 5627- 5630. (b) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646. (c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
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    • We have amply demonstrated that nucleophilic additions to nitrones derived from serine can be stereocontrolled by the appropriate choice of the protecting groups in the nitrone. See: (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 5627- 5630. (b) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646. (c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
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    • For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 179-182
    • Baldwin, S.W.1    Aube, J.2
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    • For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8037-8040
    • Langlois, N.1    Calvez, O.2    Radom, M.-O.3
  • 76
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    • For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8073-8074
    • Lubineau, A.1    Auge, J.2
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    • For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5891-5894
    • Chan, P.W.H.1    Cottrell, I.F.2    Moloney, M.G.3
  • 78
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    • See also ref 22 and references therein
    • For previous studies on Michael additions of alkyl hydroxylamines to α,β-unsaturated carbonyl compounds, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett. 1998, 1291-1293. (b) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179-182. (c) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037-8040. (d) Lubineau, A.; Auge, J. Tetrahedron Lett. 1992, 33, 8073-8074. (e) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891-5894. (f) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1848-1941. See also ref 22 and references therein.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1848-1941
    • Cardillo, G.1    Casolari, S.2    Gentilucci, L.3    Tomasini, C.4
  • 80
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    • note
    • Although it has been reported that Michael additions of N-benzylhydroxylamine are favored by the presence of water (see ref 25d), we have not observed such an effect.
  • 81
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    • In this work we use the syn/anti nomenclature according to Masamune convention. See: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557-558. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521-5523.
    • (1980) Angew. Chem., Int. Ed. Engl. , vol.19 , pp. 557-558
    • Masamune, S.1    Ali, S.A.2    Snitman, D.L.3    Garvey, D.S.4
  • 82
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    • In this work we use the syn/anti nomenclature according to Masamune convention. See: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557-558. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521-5523.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5521-5523
    • Masamune, S.1    Kaiho, T.2    Garvey, D.S.3
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    • For a discussion on the selectivity of Micahel addition to γ-alkoxy and γ-amino-α,β-unsaturated esters, see: Hanessian, S.; Sumi, K. Synthesis 1991, 1083-1089.
    • (1991) Synthesis , pp. 1083-1089
    • Hanessian, S.1    Sumi, K.2
  • 85
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    • note
    • From a preparative standpoint the obtention of mixtures of open-chain and cyclized products was inconsequential since treatment of the reaction mixture with NaOMe in MeOH afforded the desired isoxazolidin-5-ones which are easily purified by flash chromatography (see Scheme 3).
  • 90
    • 0342393038 scopus 로고    scopus 로고
    • note
    • Purification of cis and trans isomers of 16 and 18 have only analytical purposes. From a synthetic standpoint such a separation is not necessary since those compounds will be used for introducing the base through N-glycosylation.
  • 91
    • 0343698341 scopus 로고    scopus 로고
    • note
    • 2Si) can be easily prepared (6 steps) from serine in 57.7 and 51.2% overall yields, respectively. See ref 20b.
  • 92
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    • note
    • 2AlCl. See ref 19.
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    • Kocienski, P. Protecting Groups; Georg Thieme Verlag: New York, 1994; p 33.
    • (1994) Protecting Groups , pp. 33
    • Kocienski, P.1
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    • For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
    • (1982) J. Am. Chem. Soc. , vol.47 , pp. 4397-4403
    • DeShong, P.1    Dicken, M.2    Staib, R.R.3    Freyer, A.J.4    Weinreb, S.M.5
  • 102
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    • For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5598-5602
    • DeShong, P.1    Dicken, C.M.2    Leginus, J.M.3    Whittle, R.R.4
  • 103
    • 0029982336 scopus 로고    scopus 로고
    • For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
    • (1996) Tetrahedron , vol.52 , pp. 8889-8898
    • Chiacchio, U.1    Gumina, G.2    Rescifina, A.3    Romeo, R.4    Uccella, N.5    Casuscelli, F.6    Piperno, A.7    Romeo, G.8
  • 104
    • 0033601294 scopus 로고    scopus 로고
    • For 1,3-dipolar cycloadditions of nitrones with vinyl acetate, see: (a) DeShong, P.; Dicken, M.; Staib, R. R., Freyer, A. J.; Weinreb, S. M. J. Am. Chem. Soc. 1982, 47, 4397-4403. (b) DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602. (c) Chiacchio, U.; Gumina, G.; Rescifina, A.; Romeo, R.; Uccella, N.; Casuscelli, F.; Piperno, A.; Romeo, G. Tetrahedron 1996, 52, 8889-8898. (d) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9322-9327.
    • (1999) J. Org. Chem. , vol.64 , pp. 9322-9327
    • Chiacchio, U.1    Corsaro, A.2    Gumina, G.3    Rescifina, A.4    Iannazzo, D.5    Piperno, A.6    Romeo, G.7    Romeo, R.8
  • 106
    • 0342827829 scopus 로고    scopus 로고
    • note
    • Identical results were obtained when other acids (PPTS, CSA) were used.
  • 124
    • 0342827828 scopus 로고    scopus 로고
    • note
    • 2, employed for the oxidation of amino alcohols is unreliable.
  • 125
    • 0342827827 scopus 로고    scopus 로고
    • note
    • The overall yields, starting from commercial L-serine, for compound 35a were 11.0% via Michael addition route and 9.5% via nucleophilic addition route. For compound 36a the overall yields, also starting from commercial L-serine, were 7.2% via Michael addition route and 6.2% via nucleophilic addition route.
  • 126
    • 0342393031 scopus 로고    scopus 로고
    • note
    • The overall yields, starting from commercial L-serine and via 1,3-dipolar cycloaddition route, for cis compounds 45 and 46a were 10.6% and 9.2%, respectively.


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