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Volumn 65, Issue 34, 2009, Pages 6965-6971

Stereoselective syntheses of the glycosidase inhibitors hyacinthacine A2, hyacinthacine A3 and 5-epi-hyacinthacine A3

Author keywords

[No Author keywords available]

Indexed keywords

5 EPI HYACINTHACINE A3; ALKALOID; CARBON; DEXTRO SERINE; GLYCOSIDASE INHIBITOR; HYACINTHACINE A2; HYACINTHACINE A3; NITROGEN; PYRROLIZIDINE; UNCLASSIFIED DRUG;

EID: 67650531431     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.046     Document Type: Article
Times cited : (28)

References (47)
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    • For general reviews on pyrrolizidine alkaloids, see: and the previous papers in this series
    • For general reviews on pyrrolizidine alkaloids, see:. Liddell J.R. Nat. Prod. Rep. 19 (2002) 773-781 and the previous papers in this series
    • (2002) Nat. Prod. Rep. , vol.19 , pp. 773-781
    • Liddell, J.R.1
  • 3
    • 67650549659 scopus 로고    scopus 로고
    • For further reviews on the chemistry and biology of pyrrolizidine alkaloids, see
    • For further reviews on the chemistry and biology of pyrrolizidine alkaloids, see:
  • 8
    • 67650513268 scopus 로고    scopus 로고
    • For recent reviews on syntheses of this compound class
    • For recent reviews on syntheses of this compound class:
  • 11
    • 67650516735 scopus 로고    scopus 로고
    • For representative examples, see
    • For representative examples, see:
  • 16
    • 67650561130 scopus 로고    scopus 로고
    • For the use of non-sugar chiral starting materials, see for example
    • For the use of non-sugar chiral starting materials, see for example:
  • 21
    • 67650519028 scopus 로고    scopus 로고
    • For previous syntheses of hyacinthacine A2 (2) see:
    • For previous syntheses of hyacinthacine A2 (2) see:
  • 30
    • 53049084856 scopus 로고    scopus 로고
    • For a recent synthesis of radicamine B, a further pyrrolidine alkaloid which also contains the structural fragment I, see:
    • For a recent synthesis of radicamine B, a further pyrrolidine alkaloid which also contains the structural fragment I, see:. Ribes C., Falomir E., Carda M., and Marco J.A. J. Org. Chem. 73 (2008) 7779-7782
    • (2008) J. Org. Chem. , vol.73 , pp. 7779-7782
    • Ribes, C.1    Falomir, E.2    Carda, M.3    Marco, J.A.4
  • 32
    • 33846437463 scopus 로고    scopus 로고
    • In our recent synthesis of the pyrrolizidine alkaloid australine, all three C-N bonds of the heterobicyclic system were formed in a one-pot procedure:
    • In our recent synthesis of the pyrrolizidine alkaloid australine, all three C-N bonds of the heterobicyclic system were formed in a one-pot procedure:. Ribes C., Falomir E., Carda M., and Marco J.A. Org. Lett. 9 (2007) 77-80
    • (2007) Org. Lett. , vol.9 , pp. 77-80
    • Ribes, C.1    Falomir, E.2    Carda, M.3    Marco, J.A.4
  • 33
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    • Trost B.M., Fleming I., and Winterfeldt E. (Eds), Pergamon, Oxford
    • Tsuji J. In: Trost B.M., Fleming I., and Winterfeldt E. (Eds). Comprehensive Organic Synthesis Vol. 7 (1993), Pergamon, Oxford 449-468
    • (1993) Comprehensive Organic Synthesis , vol.7 , pp. 449-468
    • Tsuji, J.1
  • 36
    • 67650566306 scopus 로고    scopus 로고
    • note
    • For previous syntheses of 5-epi-3, see Refs. 5c and d.
  • 38
    • 67650531073 scopus 로고    scopus 로고
    • note
    • The compound reported in Ref. 8 (numbered 4 there) is a dehydro derivative of 19 showing an additional C{double bond, long}C bond in the side chain. In the reaction conditions described by the authors, this compound was assumed to undergo hydrogenation to 19 (numbered 5) in a neutral medium as the first step. The acid was added to the reaction medium only after this initial step had taken place.
  • 47
    • 67650522854 scopus 로고    scopus 로고
    • note
    • 7d in the range 3-11% from commercial precursors. For 3 and 5-epi-3, the sequence contains 15 steps along the respective synthetic routes 5→16→3 and 5→16→5-epi-3. The overall yields were ca. 14% and 21%, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.