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Volumn 7, Issue 18, 2005, Pages 3921-3924

De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation

Author keywords

[No Author keywords available]

Indexed keywords

DAUMONE, C ELEGANS; FATTY ACID; PALLADIUM; PHEROMONE;

EID: 24944541990     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051383e     Document Type: Article
Times cited : (78)

References (30)
  • 13
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    • We envisioned that by incorporating a late-stage ketone reduction the new route would be amenable to the incorporation of a tritium label. For similar examples of label incorporation, see: Weigel, T. M.; Liu, H.-W. Tetrahedron Lett. 1988, 29, 4221-4224.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4221-4224
    • Weigel, T.M.1    Liu, H.-W.2
  • 18
    • 0347022328 scopus 로고    scopus 로고
    • 3N (1:1 instead of 2:1) was required for the Noyori reduction of compounds with primary TBS groups; see: Li, M.; Scott, J. G.; O'Doherty, G. A. Tetrahedron Lett. 2004, 45, 1005-1009.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1005-1009
    • Li, M.1    Scott, J.G.2    O'Doherty, G.A.3
  • 19
    • 0017494276 scopus 로고
    • An Achmatowicz reaction is the oxidative rearrangement of furfuryl alcohols to 2-substituted 6-hydroxy-2H-pyran-3(6H)-ones; see: (a) Achmatowicz, O.; Bielski, R. Carbohydr. Res. 1977, 55, 165-176.
    • (1977) Carbohydr. Res. , vol.55 , pp. 165-176
    • Achmatowicz, O.1    Bielski, R.2
  • 20
    • 0034704609 scopus 로고    scopus 로고
    • For its use in carbohydrate synthesis, see: refs 5, 10, 12 and: (b) Balachari, D.; O'Doherty, G. A. Org. Lett. 2000, 2, 863-866.
    • (2000) Org. Lett. , vol.2 , pp. 863-866
    • Balachari, D.1    O'Doherty, G.A.2
  • 22
    • 0035969619 scopus 로고    scopus 로고
    • For other examples of the Noyori reduction of acylfurans, see ref 10 and: (a) Haukaas, M. H.; O'Doherty G. A. Org. Lett. 2001, 3, 3899-3992.
    • (2001) Org. Lett. , vol.3 , pp. 3899-3992
    • Haukaas, M.H.1    O'Doherty, G.A.2
  • 26
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    • note
    • 2).
  • 27
    • 0037461125 scopus 로고    scopus 로고
    • For other examples of a catalytic TEMPO oxidation to form carboxylic acids in unprotected carbohydrates see: a) Ying, L.; Gervay-Hague, J. Carbohydrate Res. 2003, 338, 835-841.
    • (2003) Carbohydrate Res. , vol.338 , pp. 835-841
    • Ying, L.1    Gervay-Hague, J.2
  • 29
    • 24944438300 scopus 로고    scopus 로고
    • note
    • D of -82 (c 0.1). Both values were measured in methanol.
  • 30
    • 24944460292 scopus 로고    scopus 로고
    • note
    • These overall yields for 1, 19, and 21 are very similar from pentynol 9 (24, 31, and 25%, respectively).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.