메뉴 건너뛰기




Volumn 126, Issue 32, 2004, Pages 10174-10182

Studies toward diazonamide A: Development of a hetero-pinacol macrocyclization cascade for the construction of the bis-macrocyclic framework of the originally proposed structure

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE SEQUENCE; HETEROCYCLIC CORE; MACROCYCLIZATION;

EID: 4043128789     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja040091q     Document Type: Article
Times cited : (59)

References (65)
  • 2
    • 0000658001 scopus 로고    scopus 로고
    • and references therein
    • Both classical, as well as milder, variants of this reaction were attempted. For leading references, see: Hennings, D. D.; Iwama, T.; Rawal, V. H. Org. Lett. 1999, 1, 1205-1208 and references therein.
    • (1999) Org. Lett. , vol.1 , pp. 1205-1208
    • Hennings, D.D.1    Iwama, T.2    Rawal, V.H.3
  • 7
    • 0001222195 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • Numerous applications of this strategy in the synthesis of complex molecules have appeared. For a representative survey, see: Davis, B. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 806-829.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 806-829
    • Davis, B.R.1    Garratt, P.J.2
  • 8
    • 0035833678 scopus 로고    scopus 로고
    • Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451-2454. For the successful application of the same approach to the revised structure of diazonamide A, see: Vedejs, E.; Zajac, M. A. Org. Lett. 2004, 6, 237-240.
    • (2001) Org. Lett. , vol.3 , pp. 2451-2454
    • Vedejs, E.1    Zajac, M.A.2
  • 9
    • 0842263582 scopus 로고    scopus 로고
    • Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451-2454. For the successful application of the same approach to the revised structure of diazonamide A, see: Vedejs, E.; Zajac, M. A. Org. Lett. 2004, 6, 237-240.
    • (2004) Org. Lett. , vol.6 , pp. 237-240
    • Vedejs, E.1    Zajac, M.A.2
  • 26
    • 0346787791 scopus 로고    scopus 로고
    • 2 in organic synthesis, see: (c) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372.
    • (2003) Tetrahedron , vol.59 , pp. 10351-10372
    • Kagan, H.B.1
  • 40
    • 0001605152 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For example, see: Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 563-611.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 563-611
    • Robertson, G.M.1
  • 41
    • 0035799896 scopus 로고    scopus 로고
    • Similar findings were presented in another diazonamide study: Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261-1264.
    • (2001) Org. Lett. , vol.3 , pp. 1261-1264
    • Wipf, P.1    Methot, J.-L.2
  • 43
    • 4043072228 scopus 로고    scopus 로고
    • note
    • This assignment is based, in part, on the fact that the alternate oxazoline would suffer from severe steric interactions with the protons from the C-11 position in ring F. Such strain also renders the approach of DAST or any other reagent from that side of the molecule quite unlikely.
  • 44
    • 4043178591 scopus 로고    scopus 로고
    • note
    • 4 at 25 °C and reflux.
  • 45
    • 0001093114 scopus 로고
    • Examples of protocols employed include: (a) Dow, R. L. J. Org. Chem. 1990, 55, 386-388.
    • (1990) J. Org. Chem. , vol.55 , pp. 386-388
    • Dow, R.L.1
  • 51
    • 4043170035 scopus 로고    scopus 로고
    • note
    • The scope of this new protocol is explored more fully in the final article in this series and has proven applicable to the formation of diverse oxazoles from ketoamides, thiazolines from thioamide-alcohols, thiazoles from ketothioamides, and furans from 1,4-dicarbonyls.
  • 52
    • 0037093942 scopus 로고    scopus 로고
    • The same operation could also be accomplished in slightly lower yield using TBAF. For an application of this alternative protocol in total synthesis, see: Jiang, W.; Wanner, J.; Lee, R. J.; Bounard, P.-Y.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5288-5290.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5288-5290
    • Jiang, W.1    Wanner, J.2    Lee, R.J.3    Bounard, P.-Y.4    Boger, D.L.5
  • 53
    • 0033564987 scopus 로고    scopus 로고
    • DEPBT: Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91-93. FDPP: Chen, S.; Xu, J. Tetrahedron Lett. 1991, 32, 6711-6714. PyBrop: Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
    • (1999) Org. Lett. , vol.1 , pp. 91-93
    • Li, H.1    Jiang, X.2    Ye, Y.-H.3    Fan, C.4    Romoff, T.5    Goodman, M.6
  • 54
    • 0025990560 scopus 로고
    • DEPBT: Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91-93. FDPP: Chen, S.; Xu, J. Tetrahedron Lett. 1991, 32, 6711-6714. PyBrop: Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6711-6714
    • Chen, S.1    Xu, J.2
  • 55
    • 0000749379 scopus 로고
    • DEPBT: Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91-93. FDPP: Chen, S.; Xu, J. Tetrahedron Lett. 1991, 32, 6711-6714. PyBrop: Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
    • (1994) J. Org. Chem. , vol.59 , pp. 2437-2446
    • Coste, J.1    Frerot, E.2    Jouin, P.3
  • 57
    • 4043094987 scopus 로고    scopus 로고
    • note
    • To achieve such a smooth rearrangement at a low temperature typically requires the presence of a protic or Lewis acid; in this case, the particular spatial arrangement of the reactive groups in 17 must facilitate this conversion as no such activators were needed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.