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Volumn , Issue 3, 2003, Pages 341-344

Synthesis of (1S,2S,3R,8S,8aR)-1,2,3,8-tetrahydroxy-6-oxa-5-thioxoindolizidine: A stable reducing swainsonine analog with controlled anomeric configuration

Author keywords

Carbohydrates; Cyclizations; Glycosidase inhibitors; Indolizidines; Swainsonine

Indexed keywords

1,2,3,8 TETRAHYDROXY 6 OXA 5 THIOXOINDOLIZIDINE; CARBOHYDRATE DERIVATIVE; INDOLIZIDINE DERIVATIVE; MANNOSE; NITROGEN; OXAZINE DERIVATIVE; SWAINSONINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037288296     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37109     Document Type: Article
Times cited : (17)

References (29)
  • 3
    • 0000727785 scopus 로고    scopus 로고
    • Ernst, B.; Hart, G. W.; Sinaÿ, P., Eds.; Wiley-VCH: Weinheim; and references therein
    • (b) Ossor, A.; Elbein, A. D. In Carbohydrates in Chemistry and Biology, Part II; Ernst, B.; Hart, G. W.; Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000, 513; and references therein.
    • (2000) Carbohydrates in Chemistry and Biology, Part II , pp. 513
    • Ossor, A.1    Elbein, A.D.2
  • 5
    • 0034721683 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (2000) Tetrahedron , vol.56 , pp. 8579
    • El Nerm, A.1
  • 6
    • 0037131706 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8543
    • Carmona, A.1    Fuentes, J.2    Robina, I.3
  • 7
    • 0036828072 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (2002) J. Org. Chem. , vol.67 , pp. 7774
    • Lindsay, K.B.1    Pyne, S.G.2
  • 8
    • 0037076936 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (2002) J. Org. Chem. , vol.67 , pp. 4325
    • Buschmann, N.1    Rueckert, A.2    Blechert, S.3
  • 9
    • 0035831144 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (2001) J. Org. Chem. , vol.66 , pp. 1761
    • Zhao, H.1    Hans, S.2    Cheng, X.3    Mootoo, D.R.4
  • 10
    • 47249110665 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (2000) Synlett , pp. 53
    • De Vicente, J.1    Gómez Arrayas, R.2    Cañada, J.3    Carretero, J.C.4
  • 11
    • 0032748320 scopus 로고    scopus 로고
    • For a recent review, see: (a) El Nerm, A. Tetrahedron 2000, 56, 8579. (b) For selected recent syntheses, see: Carmona, A.; Fuentes, J.; Robina, I. Tetrahedron Lett. 2002, 43, 8543. (c) See also: Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774. (d) See also: Buschmann, N.; Rueckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325. (e) See also: Zhao, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761. (f) See also: De Vicente, J.; Gómez Arrayas, R.; Cañada, J.; Carretero, J. C. Synlett 2000, 53. (g) See also: Trost, B. M.; Patterson, D. E. Chem.-Eur. J. 1999, 5, 3279.
    • (1999) Chem.-Eur. J. , vol.5 , pp. 3279
    • Trost, B.M.1    Patterson, D.E.2
  • 21
    • 0013534325 scopus 로고    scopus 로고
    • note
    • Notice that, although the stereochemical notation at C-2 and C-8 changes from 1 to 4, the absolute stereochemistry remains identical at these centers.
  • 27
    • 0013525914 scopus 로고    scopus 로고
    • note
    • 5S).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.