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Volumn , Issue 22, 2007, Pages 2211-2221

Cascading pericyclic reactions: Building complex carbon frameworks for natural product synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMISININ; CARBON; DITERPENE; NATURAL PRODUCT;

EID: 34249780109     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b700054p     Document Type: Article
Times cited : (61)

References (85)
  • 20
    • 0001049011 scopus 로고
    • and references therein They observed that electron-rich double bonds cause the anionic oxy-Cope reaction to decelerate, see:
    • K. Rajagopalan S. Janardhanam A. Balakumar J. Org. Chem. 1993 58 5482
    • (1993) J. Org. Chem. , vol.58 , pp. 5482
    • Rajagopalan, K.1    Janardhanam, S.2    Balakumar, A.3
  • 32
    • 34249825152 scopus 로고    scopus 로고
    • University of Ottawa
    • D. Deon, MSc thesis, University of Ottawa, 2001
    • (2001)
    • Deon Msc Thesis, D.1
  • 34
    • 0032560097 scopus 로고    scopus 로고
    • The natural enantiomer is actually (-)-arteannuin M, whose absolute configuration we assigned through its total synthesis
    • G. D. Brown L.-K. Sy R. Haynes Tetrahedron 1998 54 4345
    • (1998) Tetrahedron , vol.54 , pp. 4345
    • Brown, G.D.1    Sy, L.-K.2    Haynes, R.3
  • 37
    • 0003942864 scopus 로고
    • Wiley-Interscience, New York, Microwave heating was found to be more desirable compared to conventional heating methods, with our cascading reaction sequences occurring with a 10-300 fold increase in rate under these conditions. For reviews on the use of microwaves in organic synthesis, see:
    • E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994
    • (1994) Stereochemistry of Organic Compounds
    • Eliel, E.L.1    Wilen, S.H.2
  • 43
    • 34249828627 scopus 로고    scopus 로고
    • All reactions were performed in toluene, using different additives as noted above depending on the purpose of the experiment
    • All reactions were performed in toluene, using different additives as noted above depending on the purpose of the experiment
  • 44
    • 34249792326 scopus 로고    scopus 로고
    • 3N, pyridine, 2,6-di-tert- butylpyridine, DMAP, sparteine and 2-tert-butyl-1,1,3,3-tetramethylguanidine
    • 3N, pyridine, 2,6-di-tert- butylpyridine, DMAP, sparteine and 2-tert-butyl-1,1,3,3-tetramethylguanidine
  • 45
    • 34249811456 scopus 로고    scopus 로고
    • Conditions: KHMDS, DME, 110°C. Quench with AcOH to isolate the macrocyclic ketone, the precursor for the ene reaction in the thermal sequence
    • Conditions: KHMDS, DME, 110°C. Quench with AcOH to isolate the macrocyclic ketone, the precursor for the ene reaction in the thermal sequence
  • 72
    • 3142769156 scopus 로고    scopus 로고
    • Seminal work in the field of diastereoselective control through macrocyclic conformation was performed by W. C. Still et al., see:
    • E. L. O. Sauer L. Barriault J. Am. Chem. Soc. 2004 126 8569
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8569
    • Sauer, E.L.O.1    Barriault, L.2
  • 79
    • 0022578985 scopus 로고
    • There is a wealth of experimental evidence supporting this mechanism; however it is impossible to include all results in a review: key ideas have therefore been presented. A full account of the results leading to these conclusions can be found in ref. 32 and
    • W. C. Still A. G. Romero J. Am. Chem. Soc. 1986 108 2105
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 2105
    • Still, W.C.1    Romero, A.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.