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Volumn , Issue 25, 2008, Pages 2870-2872

Formal total synthesis of (-)-haouamine A

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BENZALDEHYDE DERIVATIVE; CARBON; FLUORIDE; HAOUAMINE A; PHOSPHONIC ACID DERIVATIVE; RHODIUM;

EID: 45549085402     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b805295f     Document Type: Article
Times cited : (57)

References (38)
  • 6
    • 33645450011 scopus 로고    scopus 로고
    • For a modified approach and the synthesis of the non-natural enantiomer (+)- 1, see:
    • P. S. Baran N. Z. Burns J. Am. Chem. Soc. 2006 128 3908
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 3908
    • Baran, P.S.1    Burns, N.Z.2
  • 13
    • 0037067104 scopus 로고    scopus 로고
    • The use of in situ generated ylide invariably led to lower yields and various degree of epimerization; the procedure described in the following publication was used to prepare the ylide:
    • A. Endo A. Yanagisawa M. Abe S. Tohma T. Kan T. Fukuyama J. Am. Chem. Soc. 2002 124 6552
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6552
    • Endo, A.1    Yanagisawa, A.2    Abe, M.3    Tohma, S.4    Kan, T.5    Fukuyama, T.6
  • 22
    • 20544450502 scopus 로고    scopus 로고
    • A. de Meijere and. F. Diederich. Wiley-VCH. Weinheim, 2nd edn. p. 217. Other protocols afforded appreciable amounts of the corresponding saturated ketone rather than the desired enone. Under the optimized conditions, however, the enone: ketone ratio was invariably greater than 10: 1. For a discussion see:
    • S. Bräse and A. de Meijere, in Metal-Catalyzed Cross-Coupling Reactions, ed., A. de Meijere, and, F. Diederich,, Wiley-VCH, Weinheim, 2nd edn, 2004, vol. 1, p. 217
    • (2004) Metal-Catalyzed Cross-Coupling Reactions, Ed.
    • Bräse, S.1    De Meijere In, A.2
  • 26
    • 0001026255 scopus 로고
    • 2 at -78°C, a ∼1: 1 mixture of the two possible enol triflates is formed. This result suggests that the selective formation of compound 23 under the chosen conditions is mostly thermodynamic in origin
    • M. E. Garst J. N. Bonfiglio D. A. Grudoski J. Marks J. Org. Chem. 1980 45 2307
    • (1980) J. Org. Chem. , vol.45 , pp. 2307
    • Garst, M.E.1    Bonfiglio, J.N.2    Grudoski, D.A.3    Marks, J.4
  • 30
    • 33845376366 scopus 로고
    • The rather poor yield in this step is ascribed to the low stability of the pyrone entities of 27 and 28 in refluxing toluene
    • W. J. Scott J. K. Stille J. Am. Chem. Soc. 1986 108 3033
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3033
    • Scott, W.J.1    Stille, J.K.2
  • 38
    • 45549096617 scopus 로고    scopus 로고
    • 10.1039/b805299a. (accompanying paper). Attempts to reproduce the end game did afford the desired product but the yields were much lower than those reported in the literature, despite considerable experimentation. However, the small amounts of product allowed us to confirm the absolute configuration assigned to (-)-. 1 by comparison with an authentic sample. The two known asymmetric syntheses of the key intermediate. 25 compare as follows: . . . . . . . . . . . . . .
    • A. Fürstner J.-A. Funel M. Tremblay L. C. Bouchez C. Nevado J. Ackerstaff C. C. Stimson Chem. Commun. 2008 10.1039/b805299a
    • (2008) Chem. Commun.
    • Fürstner, A.1    Funel, J.-A.2    Tremblay, M.3    Bouchez, L.C.4    Nevado, C.5    Ackerstaff, J.6    Stimson, C.C.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.