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Volumn 130, Issue 38, 2008, Pages 12630-12631

A stereoselective synthesis of (+)-gonyautoxin 3

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALDEHYDE; ALKENE; AZIRIDINE; GONYAUTOXIN; GUANIDINE; NEOSAXITOXIN; SAXITOXIN; SODIUM CHANNEL;

EID: 52449117715     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805651g     Document Type: Article
Times cited : (79)

References (31)
  • 2
    • 33645393913 scopus 로고    scopus 로고
    • For leading reviews, see: a
    • For leading reviews, see: (a) Llewellyn, L. E. Nat. Prod. Rep. 2006, 23, 200-222.
    • (2006) Nat. Prod. Rep , vol.23 , pp. 200-222
    • Llewellyn, L.E.1
  • 5
    • 11244296111 scopus 로고    scopus 로고
    • and references therein
    • (b) Tikhonov, D. B.; Zhorov, B. S. Biophys. J. 2005, 88, 184-197, and references therein.
    • (2005) Biophys. J , vol.88 , pp. 184-197
    • Tikhonov, D.B.1    Zhorov, B.S.2
  • 7
    • 0000901167 scopus 로고
    • (b) Kishi, Y. Heterocycles 1980, 14, 1477-1495.
    • (1980) Heterocycles , vol.14 , pp. 1477-1495
    • Kishi, Y.1
  • 12
    • 0000796911 scopus 로고    scopus 로고
    • Following their earlier report, Kishi et al. have described an asymmetric synthesis of (-)-decarbamoylsaxitoxin; see: (g) Hong, C. Y.; Kishi, Y. J. Am. Chem. Soc. 1992, 114, 7001-7006.
    • Following their earlier report, Kishi et al. have described an asymmetric synthesis of (-)-decarbamoylsaxitoxin; see: (g) Hong, C. Y.; Kishi, Y. J. Am. Chem. Soc. 1992, 114, 7001-7006.
  • 17
    • 0021041317 scopus 로고    scopus 로고
    • An approach to GTX 2 and 3 has been described, see: Hannick, S. M, Kishi, Y. J. Org. Chem. 1983, 48, 3833-3835
    • An approach to GTX 2 and 3 has been described, see: Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833-3835.
  • 19
    • 4644238043 scopus 로고    scopus 로고
    • Analogous oxidation reactions with indole derivatives give evidence for a zwitterionic intermediate; see: Padwa, A, Flick, A. C, Leverett, C. A, Stengel, T. J. Org. Chem. 2004, 69, 6377-6386
    • Analogous oxidation reactions with indole derivatives give evidence for a zwitterionic intermediate; see: Padwa, A.; Flick, A. C.; Leverett, C. A.; Stengel, T. J. Org. Chem. 2004, 69, 6377-6386.
  • 21
    • 52449114434 scopus 로고    scopus 로고
    • An X-ray crystal structure of a modified form of this intermediate confirms the trans stereochemical assignment
    • An X-ray crystal structure of a modified form of this intermediate confirms the trans stereochemical assignment.
  • 22
    • 52449109360 scopus 로고    scopus 로고
    • 2 is likely responsible for the reduced isolated yields.
    • 2 is likely responsible for the reduced isolated yields.
  • 23
    • 52449103147 scopus 로고    scopus 로고
    • 2 being the only medium in which complete consumption of the starting guanidine 7 is observed.
    • 2 being the only medium in which complete consumption of the starting guanidine 7 is observed.
  • 25
    • 52449103992 scopus 로고    scopus 로고
    • Hexavalent chromium, TEMPO, and DMSO-based oxidation protocols universally consumed starting material without generating ketone 12.
    • Hexavalent chromium, TEMPO, and DMSO-based oxidation protocols universally consumed starting material without generating ketone 12.
  • 30
    • 41249086158 scopus 로고    scopus 로고
    • An attempt to utilize guanidine C-H insertion for assembling bromopyrrole-derived natural products has been described; see: (a) Wang, S, Romo, D. Angew. Chem, Int. Ed. 2008, 47, 1284-1286
    • An attempt to utilize guanidine C-H insertion for assembling bromopyrrole-derived natural products has been described; see: (a) Wang, S.; Romo, D. Angew. Chem., Int. Ed. 2008, 47, 1284-1286.
  • 31
    • 34548640751 scopus 로고    scopus 로고
    • For a recent review of this family of molecules, see:b
    • For a recent review of this family of molecules, see:(b) Köck, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem., Int. Ed. 2007, 46, 6586-6594.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 6586-6594
    • Köck, M.1    Grube, A.2    Seiple, I.B.3    Baran, P.S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.