메뉴 건너뛰기




Volumn 21, Issue 40, 2015, Pages 13900-13903

Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations

Author keywords

asymmetric synthesis; boron; iterative homologation; mycolactone; natural products

Indexed keywords

BORON;

EID: 84941809133     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201503122     Document Type: Article
Times cited : (24)

References (65)
  • 15
    • 0004321816 scopus 로고    scopus 로고
    • in. (Eds K. Asiedu, R. Scherpbier, M. C. Raviglione), Geneva World Health Organization, WHO/CDS/GBUI/, - 60.
    • K. Asiedu, S. Etuaful, in Buruli ulcer: Mycobacterium ulcerans infection. (Eds K. Asiedu, R. Scherpbier, M. C. Raviglione), Geneva World Health Organization, 2000, WHO/CDS/GBUI/ 2000.1, pp. - 60.
    • (2000) Buruli Ulcer: Mycobacterium Ulcerans Infection , pp. 20001
    • Asiedu, K.1    Etuaful, S.2
  • 39
    • 84941803943 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 2982.
    • (2006) Angew. Chem. , vol.118 , pp. 2982
  • 42
    • 84901593487 scopus 로고    scopus 로고
    • For a review on lithiation-borylation chemistry see
    • Angew. Chem. 2007, 119, 7635; For a review on lithiation-borylation chemistry see:
    • (2007) Angew. Chem. , vol.119 , pp. 7635
  • 45
    • 84941807602 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 4471;
    • (2014) Angew. Chem. , vol.126 , pp. 4471
  • 47
    • 84941810164 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 2563;
    • (2013) Angew. Chem. , vol.125 , pp. 2563
  • 52
    • 84941803664 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 5658;
    • (2014) Angew. Chem. , vol.126 , pp. 5658
  • 54
    • 84941802748 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 6435.
    • (2009) Angew. Chem. , vol.121 , pp. 6435
  • 56
    • 84941811696 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 12612;
    • (2012) Angew. Chem. , vol.124 , pp. 12612
  • 61
    • 84941808044 scopus 로고    scopus 로고
    • Through submersion of the needle tip into the solution ensures low temperature addition of the organolithium to the reaction mixture.
    • Through submersion of the needle tip into the solution ensures low temperature addition of the organolithium to the reaction mixture.
  • 63
    • 84941803714 scopus 로고    scopus 로고
    • The less stable Grubbs 2nd generation catalyst formed more of 21 (20 % conversion) in the same reaction time, supporting this inference.
    • The less stable Grubbs 2nd generation catalyst formed more of 21 (20 % conversion) in the same reaction time, supporting this inference.
  • 64
    • 84941811262 scopus 로고    scopus 로고
    • Structure of diene 22, see Supporting Information for full characterization.
    • Structure of diene 22, see Supporting Information for full characterization.
  • 65
    • 84941805950 scopus 로고    scopus 로고
    • Accurate assessment of the d.r. associated with the final homologation was not possible because of the presence of minor diastereomers associated with epimers at C13, C5 and C6. However, based on previous homologations with primary carbamates (and supported by the 13C NMR), we expect the d.r. of the final homologation reaction to be >95:5. See Supporting Information for full details.
    • Accurate assessment of the d.r. associated with the final homologation was not possible because of the presence of minor diastereomers associated with epimers at C13, C5 and C6. However, based on previous homologations with primary carbamates (and supported by the 13C NMR), we expect the d.r. of the final homologation reaction to be >95:5. See Supporting Information for full details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.