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Volumn 10, Issue 17, 2008, Pages 3781-3784

Pinacol macrocyclization-based route to the polyfused medium-sized CDE ring system of lancifodilactone G

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOCTANE DERIVATIVE; IODIDE; LANCIFODILACTONE G; MACROCYCLIC COMPOUND; SAMARIUM; SAMARIUM DIIODIDE; TRITERPENE;

EID: 55949100808     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8014607     Document Type: Article
Times cited : (41)

References (36)
  • 6
    • 0002460703 scopus 로고
    • For reviews of medium-sized ring synthesis, see: a
    • For reviews of medium-sized ring synthesis, see: (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
    • (1981) Acc. Chem. Res , vol.14 , pp. 95
    • Illuminati, G.1    Mandolini, L.2
  • 8
    • 0026721571 scopus 로고
    • For reviews of eight-membered ring carbocycle construction, see: a
    • For reviews of eight-membered ring carbocycle construction, see: (a) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
    • (1992) Tetrahedron , vol.48 , pp. 5757
    • Petasis, N.A.1    Patane, M.A.2
  • 16
    • 61349157774 scopus 로고    scopus 로고
    • For thermal Claisen ring expansion for synthesis of the CDEF ring system of 1, see: Paquette, L. A.; Lai, K. W. Heterocycles 2009, accepted.
    • For thermal Claisen ring expansion for synthesis of the CDEF ring system of 1, see: Paquette, L. A.; Lai, K. W. Heterocycles 2009, accepted.
  • 17
    • 61349190793 scopus 로고    scopus 로고
    • For previous applications of Claisen ring expansion for construction of eight-membered ring systems from our laboratory, see: (a) Paquette, L. A. In Stereocontrolled Organic Synthesis; Trost, B. M, Ed, Blackwell Scientific Publications: Oxford, England, 1994; pp 313-336
    • For previous applications of Claisen ring expansion for construction of eight-membered ring systems from our laboratory, see: (a) Paquette, L. A. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell Scientific Publications: Oxford, England, 1994; pp 313-336.
  • 25
    • 3543057490 scopus 로고    scopus 로고
    • 2-mediated reactions, see: (a) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371.
    • 2-mediated reactions, see: (a) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371.
  • 26
    • 0346787791 scopus 로고    scopus 로고
    • 2 chemistry, see: Kagan, H. B. Tetrahedron 2003, 59, 10351.
    • 2 chemistry, see: Kagan, H. B. Tetrahedron 2003, 59, 10351.
  • 27
    • 20544467704 scopus 로고    scopus 로고
    • The only report that utilizes the pinacol macrocyclization of dialdehydes is found in the synthesis of a C8-carbasugar. See: Andriuzzi, O, Gravier-Pelletier, C, Vogel, P, Merrer, V. L. Tetrahedron 2005, 61, 7094
    • The only report that utilizes the pinacol macrocyclization of dialdehydes is found in the synthesis of a C8-carbasugar. See: Andriuzzi, O.; Gravier-Pelletier, C.; Vogel, P.; Merrer, V. L. Tetrahedron 2005, 61, 7094.
  • 29
    • 0035905441 scopus 로고    scopus 로고
    • For a review of the B-alkyl Suzuki-Miyaura reaction in natural product synthesis, see: (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
    • For a review of the B-alkyl Suzuki-Miyaura reaction in natural product synthesis, see: (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
  • 30
    • 0000110272 scopus 로고    scopus 로고
    • Apart from inducing the gem-dimethyl effect, the quaternary carbon center at C-13 (ref 18) in 6 was intended to impose a steric environment comparable to that in 1. For the gem-dimethyl effect, see: (a) Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701.
    • Apart from inducing the gem-dimethyl effect, the quaternary carbon center at C-13 (ref 18) in 6 was intended to impose a steric environment comparable to that in 1. For the gem-dimethyl effect, see: (a) Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701.
  • 36
    • 61349092116 scopus 로고    scopus 로고
    • In contrast to Inanaga' s work (ref 16a), we found that no chelating agent such as DMAE (N,N-dimethylaminoethanol) is required to suppress the formation of the unwanted α-hydroxy ester.
    • In contrast to Inanaga' s work (ref 16a), we found that no chelating agent such as DMAE (N,N-dimethylaminoethanol) is required to suppress the formation of the unwanted α-hydroxy ester.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.