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Volumn 2, Issue 23, 2000, Pages 3731-3734

Asymmetric synthesis of the fully functional macrolide core of salicylihalamide: Remote control of olefin geometry during RCM

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FUSED HETEROCYCLIC RINGS; SALICYLIHALAMIDE A;

EID: 0034676533     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006646d     Document Type: Article
Times cited : (124)

References (67)
  • 12
    • 0000785058 scopus 로고    scopus 로고
    • Recent reviews: (a) Fürstner, A. Angew. Chem. 2000, 112, 3140; Angew. Chem., Int. Ed. 2000, 39, 3012.
    • (2000) Angew. Chem. , vol.112 , pp. 3140
    • Fürstner, A.1
  • 13
    • 0001399412 scopus 로고    scopus 로고
    • Recent reviews: (a) Fürstner, A. Angew. Chem. 2000, 112, 3140; Angew. Chem., Int. Ed. 2000, 39, 3012.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3012
  • 15
  • 16
    • 0030771019 scopus 로고    scopus 로고
    • (c) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2036
  • 41
    • 0033620417 scopus 로고    scopus 로고
    • These "second generation" metathesis catalysts have been independently and almost simultaneously reported by three groups, cf.: (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2674
    • Huang, J.1    Stevens, E.D.2    Nolan, S.P.3    Petersen, J.L.4
  • 49
    • 0042801363 scopus 로고    scopus 로고
    • note
    • It is important to quench the reaction mixture by addition of ethyl vinyl ether in order to inactivate the catalyst prior to workup.
  • 53
    • 0034674252 scopus 로고    scopus 로고
    • For a pertinent review on how branches on an acyclic compound affect the conformation, see: Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2054 and literature cited therein. We have briefly studied if changing the relative configuration between the Me and the OMOM branch of the cyclization precursor from anti to syn has an influence on the stereochemical outcome of RCM but found no appreciable effect. Details will be reported in a forthcoming full paper.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2054
    • Hoffmann, R.W.1
  • 54
    • 0038206375 scopus 로고    scopus 로고
    • For a previous example of the influence of remote substituents on the stereochemical course of RCM. see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942.
    • (1996) J. Org. Chem. , vol.61 , pp. 3942
    • Fürstner, A.1    Langemann, K.2
  • 56
    • 0042801362 scopus 로고    scopus 로고
    • note
    • We believe that the cyclizations reported herein provide a unique opportunity to reach a better understanding of the transition state of RCM reactions because (i) mechanistically well behaved catalysts are employed, (ii) the substrates have a defined site of initiation (the terminal rather than the trisubstituted alkene), and (iii) the strong stereochemical preferences allow to match the results by molecular modeling. Theoretical investigations along these lines are underway.
  • 57
    • 0001645448 scopus 로고    scopus 로고
    • Another explanaton for the different stereoselectivity in RCM of the O-protected substrates (23b-d) as compared to the O-unprotected diene 23a relates to the possible in situ formation of phenolate substituted metathesis catalysts in the latter case. Such compounds are known to be catalytically active (cf: Chang, S.; Jones, L.; Wang, C.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 3460). We thank the referee for pointing out this possibility which is presently studied in our laboratory.
    • (1998) Organometallics , vol.17 , pp. 3460
    • Chang, S.1    Jones, L.2    Wang, C.3    Henling, L.M.4    Grubbs, R.H.5
  • 58
    • 0000775011 scopus 로고    scopus 로고
    • Thus far, only macrocyclic (Z)-alkenes can be selectively and predicatably formed by metathesis via a new protocol comprising alkyne metathesis followed by Lindlar reduction, cf.: (a) Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. 1998, 37, 1734.
    • (1998) Angew. Chem. , vol.110 , pp. 1758
    • Fürstner, A.1    Seidel, G.2
  • 59
    • 0038731101 scopus 로고    scopus 로고
    • Thus far, only macrocyclic (Z)-alkenes can be selectively and predicatably formed by metathesis via a new protocol comprising alkyne metathesis followed by Lindlar reduction, cf.: (a) Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. 1998, 37, 1734.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1734
  • 62
  • 63
    • 0038584256 scopus 로고    scopus 로고
    • (d) Fürstner, A.; Grela, K. Angew. Chem. 2000, 112, 1292; Angew. Chem., Int. Ed. 2000, 39, 1234.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1234
  • 67
    • 0038542691 scopus 로고    scopus 로고
    • For a discussion, see: Fürstner, A. Synlett 1999, 1523.
    • (1999) Synlett , pp. 1523
    • Fürstner, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.