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Volumn 58, Issue , 2002, Pages 421-430

A synthesis of (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidinedioxy)indolizidin-5-one from D-ribose: Improved access to (-)-swainsonine and its analogs

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXY 1,2 (ISOPROPYLIDINEDIOXY)INDOLIZIDIN 5 ONE; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; LACTAM DERIVATIVE; RIBOSE; SWAINSONINE; SWAINSONINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037159762     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s(m)40     Document Type: Article
Times cited : (29)

References (37)
  • 14
    • 0035831144 scopus 로고    scopus 로고
    • Dozens of syntheses of swainsonine have been published; too many to review here. For a recent example, see H. Zhao, S. Hans, X. Cheng, and D. R. Mootoo, J. Org. Chem., 2001, 66, 1761. For a review of the synthesis of swainsonine and its analogs, see A. El Nemr, Tetrahedron, 2000, 56, 8579.
    • (2001) J. Org. Chem. , vol.66 , pp. 1761
    • Zhao, H.1    Hans, S.2    Cheng, X.3    Mootoo, D.R.4
  • 15
    • 0034721683 scopus 로고    scopus 로고
    • Dozens of syntheses of swainsonine have been published; too many to review here. For a recent example, see H. Zhao, S. Hans, X. Cheng, and D. R. Mootoo, J. Org. Chem., 2001, 66, 1761. For a review of the synthesis of swainsonine and its analogs, see A. El Nemr, Tetrahedron, 2000, 56, 8579.
    • (2000) Tetrahedron , vol.56 , pp. 8579
    • El Nemr, A.1
  • 17
    • 0011789337 scopus 로고
    • U. S. Patent 5,023,340, 1991
    • G. W. J. Fleet, U. S. Patent 5,023,340, 1991 (Chem. Abstr., 1991, 115, 136472).
    • (1991) Chem. Abstr. , vol.115 , pp. 136472
    • Fleet, G.W.J.1
  • 20
    • 0011731476 scopus 로고    scopus 로고
    • U. S. Patent 5,919,952, 1999
    • W. H. Pearson and E. J. Hembre, U. S. Patent 5,919,952, 1999 (Chem. Abstr., 1999, 131, 73836).
    • (1999) Chem. Abstr. , vol.131 , pp. 73836
    • Pearson, W.H.1    Hembre, E.J.2
  • 21
    • 0030787335 scopus 로고    scopus 로고
    • For related work on analogs of swainsonine, see ref. 13 above and: (a) E. J. Hembre and W. H. Pearson, Tetrahedron, 1997, 53, 11021.
    • (1997) Tetrahedron , vol.53 , pp. 11021
    • Hembre, E.J.1    Pearson, W.H.2
  • 26
    • 0017309494 scopus 로고
    • Stork and Raucher added vinylmagnesium bromide to 2,3-isopropylidene-L-erythrose, then carried out a Johnson orthoester Claisen rearrangement on the resultant allylic alcohol in a fashion similar to the strategy we have used in the current work. They did not study the stereoselectivity of the Grignard reaction. See: G. Stork and Raucher, J. Am. Chem. Soc., 1976, 98, 1583.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 1583
    • Stork, G.1    Raucher2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.