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Volumn 11, Issue 16, 2009, Pages 3690-3693

Highly efficient borylation Suzuki coupling process for 4-bromo-2-ketothiazoles: Straightforward access to micrococcinate and saramycetate esters

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ESTER; PALLADIUM; THIAZOLE DERIVATIVE;

EID: 68949113487     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901525t     Document Type: Article
Times cited : (45)

References (36)
  • 7
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    • For recent total synthesis of thiopeptides, see: a
    • For recent total synthesis of thiopeptides, see: (a) Lefranc, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2009, 48, 4198-4201.
    • (2009) Angew. Chem., Int. Ed , vol.48 , pp. 4198-4201
    • Lefranc, D.1    Ciufolini, M.A.2
  • 16
    • 15444375711 scopus 로고    scopus 로고
    • First synthesis of a heterocyclic core of a thiopeptide antibiotic (GE2270A) in a complete cross-coupling approach: Heckmann, G.; Bach, T. Angew. Chem., Int. Ed 2005, 44, 1199-1201.
    • (c) First synthesis of a heterocyclic core of a thiopeptide antibiotic (GE2270A) in a complete cross-coupling approach: Heckmann, G.; Bach, T. Angew. Chem., Int. Ed 2005, 44, 1199-1201.
  • 19
    • 68949143562 scopus 로고    scopus 로고
    • Direct palladium-catalyzed stannylation of 4a using bistrimethystannane is penalized by the side production of 2,2′-acetyl-4, 4′-bithiazole (35% GC yield), which could not be isolated from the expected 2-acetylthiazol-4-ylstannane (51% GC yield).
    • (c) Direct palladium-catalyzed stannylation of 4a using bistrimethystannane is penalized by the side production of 2,2′-acetyl-4, 4′-bithiazole (35% GC yield), which could not be isolated from the expected 2-acetylthiazol-4-ylstannane (51% GC yield).
  • 21
    • 10044267764 scopus 로고    scopus 로고
    • For palladium-catalyzed borylation of aromatics methods using pinacolborane, see: a
    • For palladium-catalyzed borylation of aromatics methods using pinacolborane, see: (a) Broutin, P.-E.; Cerna, I.; Campaniello, M.; Leroux, F.; Colobert, F. Org. Lett. 2004, 6, 4419-4422.
    • (2004) Org. Lett , vol.6 , pp. 4419-4422
    • Broutin, P.-E.1    Cerna, I.2    Campaniello, M.3    Leroux, F.4    Colobert, F.5
  • 24
    • 34447569410 scopus 로고    scopus 로고
    • For palladium-catalyzed borylation of aromatics methods using bis(pinacol)borane, see: a
    • For palladium-catalyzed borylation of aromatics methods using bis(pinacol)borane, see: (a) Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359-5363.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 5359-5363
    • Billingsley, K.L.1    Barder, T.E.2    Buchwald, S.L.3
  • 31
    • 68949121347 scopus 로고    scopus 로고
    • Both borylated thiazoles 8a, b proved to be highly unstable under usual isolating procedures.
    • Both borylated thiazoles 8a, b proved to be highly unstable under usual isolating procedures.
  • 33
    • 34548269107 scopus 로고    scopus 로고
    • Bagley and co-workers recently reported the first and unique synthesis of ethyl saramycetate in 8 steps and 11% overyield from diethoxyacetonitrile: Glover, C.; Merritt, E. A.; Bagley, M. C. Tetrahedron Lett. 2007, 48, 7027-7030.
    • Bagley and co-workers recently reported the first and unique synthesis of ethyl saramycetate in 8 steps and 11% overyield from diethoxyacetonitrile: Glover, C.; Merritt, E. A.; Bagley, M. C. Tetrahedron Lett. 2007, 48, 7027-7030.
  • 34
    • 0037047241 scopus 로고    scopus 로고
    • For a general access to 2′-substituted 4-bromo-2,4′- bithiazoles using regioselective Negishi and Stille cross-coupling reactions, see: Bach, T.; Heuser, S. J. Org. Chem. 2002, 67, 5789-5795.
    • For a general access to 2′-substituted 4-bromo-2,4′- bithiazoles using regioselective Negishi and Stille cross-coupling reactions, see: Bach, T.; Heuser, S. J. Org. Chem. 2002, 67, 5789-5795.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.