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Volumn 25, Issue 14, 2014, Pages 2025-2029

A metathesis-acylation approach to the bicyclic core of polycyclic poly-prenylated acylphloroglucinols

Author keywords

alkene acylation; bicyclic compounds; metathesis; natural products; steric hindrance

Indexed keywords

ALKENE DERIVATIVE; BICYCLO[3.3.1]NONAN 9 ONE; BICYCLO[3.3.1]NONANE DERIVATIVE; CLUSIANONE; CYCLOOCTENE; GARSUBELLIN A; HYPERFORIN; NEMOROSONE; PHLOROGLUCINOL DERIVATIVE; POLYCYCLIC HYDROCARBON; POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84906791185     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1378380     Document Type: Article
Times cited : (6)

References (95)
  • 1
    • 33749844000 scopus 로고    scopus 로고
    • For an excellent review concerning the various types of PPAPs, see: Ciochina R., Grossman R. Chem. Rev.: 2006; 106 3963
    • (2006) Chem. Rev. , vol.106 , pp. 3963
    • Ciochina, R.1    Grossman, R.2
  • 35
    • 23744504437 scopus 로고    scopus 로고
    • The starting acyl cyanide was prepared according to
    • The starting acyl cyanide was prepared according to: Jung M. E., Min S.-J. J. Am. Chem. Soc.: 2005; 127 10834
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10834
    • Jung, M.E.1    Min, S.-J.2
  • 37
    • 84906790395 scopus 로고
    • In aldol adducts where the chiral carbon between the carbonyl group and the hydroxy group contains a bulky substituent, the syn isomer shows a larger coupling constant than the anti isomer, e.g. see
    • In aldol adducts where the chiral carbon between the carbonyl group and the hydroxy group contains a bulky substituent, the syn isomer shows a larger coupling constant than the anti isomer, e.g., see: Heng K. K., Simpson J., Smith R. A. J, Robinson W. T. J. Org. Chem.: 1981; 46 2032
    • (1981) J. Org. Chem. , vol.46 , pp. 2032
    • Heng, K.K.1    Simpson, J.2    Smith, R.A.J.3    Robinson, W.T.4
  • 40
    • 84906790837 scopus 로고    scopus 로고
    • Our stereochemical assignment is in full agreement with the X-ray structure depicted in ref. 15. For other examples of aldol reactions of sterically congested ester enolates with aldehydes, see
    • Our stereochemical assignment is in full agreement with the X-ray structure depicted in ref. 15. For other examples of aldol reactions of sterically congested ester enolates with aldehydes, see
  • 45
    • 0001015873 scopus 로고
    • ® as a base in alkylation reactions of sensitive aldol adducts was reported in
    • ® as a base in alkylation reactions of sensitive aldol adducts was reported in: Diem M. J., Burow D. F., Fry J. L. J. Org. Chem.: 1977; 42 1801
    • (1977) J. Org. Chem. , vol.42 , pp. 1801
    • Diem, M.J.1    Burow, D.F.2    Fry, J.L.3
  • 48
    • 0026721571 scopus 로고
    • For a general review of the synthesis of eight-membered carbocycles, see
    • For a general review of the synthesis of eight-membered carbocycles, see: Petasis N. A., Patane M. A. Tetrahedron: 1992; 48 5757
    • (1992) Tetrahedron , vol.48 , pp. 5757
    • Petasis, N.A.1    Patane, M.A.2
  • 49
    • 0034674322 scopus 로고    scopus 로고
    • Angew. Chem. 2000, 112, 2153
    • Maier M. E. Angew. Chem. Int. Ed.: 2000; 39 2073; Angew. Chem. 2000, 112, 2153
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2073
    • Maier, M.E.1
  • 66
    • 84906790209 scopus 로고    scopus 로고
    • In a related RCM reaction with the Grubbs II catalyst (Scheme 6), we also observed acceleration exerted by a geminal dimethyl arrangement (Feidt, E. unpublished results). For the RCM of 1,9-decadiene into cyclooctene, see
    • In a related RCM reaction with the Grubbs II catalyst (Scheme 6), we also observed acceleration exerted by a geminal dimethyl arrangement (Feidt, E. unpublished results). For the RCM of 1,9-decadiene into cyclooctene, see
  • 72
    • 84906791514 scopus 로고    scopus 로고
    • 3.
    • 14b The final refinement resulted in: R 1 = 0.036. Crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Copies of the data can be obtained free of charge on quoting the deposition number CCDC 990861 (www.ccdc.cam.ac.uk/data-request/cif).
  • 80
    • 84906790210 scopus 로고
    • For additional details, see: US Patent 3524884; Chem. Abstr. 1970, 73, 87533.
    • For additional details, see: Kretschmar H. C. US Patent 3524884: 1970;; Chem. Abstr. 1970, 73, 87533.
    • (1970)
    • Kretschmar, H.C.1
  • 84
    • 0009896481 scopus 로고
    • For an analogous reaction giving a bicyclo[3.2.1]octan-8-one skeleton, see
    • For an analogous reaction giving a bicyclo[3.2.1]octan-8-one skeleton, see: Nelsen S. F., Kapp D. L. J. Am. Chem. Soc.: 1986; 108 1265
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1265
    • Nelsen, S.F.1    Kapp, D.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.