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Volumn 54, Issue 27, 1998, Pages 7907-7918

A convergent enantioselective total synthesis of (-)- perhydrohistrionicotoxin with an intramolecular imino ene-type reaction as a key step

Author keywords

Alkaloids; Asymmetric synthesis; Imines; Spiro compounds

Indexed keywords

ALKALOID; IMINE; NEUROTOXIN; PERHYDROHISTRIONICOTOXIN; SPIRO COMPOUND;

EID: 0032474797     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00425-6     Document Type: Article
Times cited : (47)

References (45)
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    • 2. Reviews: (a) Daly, J. W. in Progress in the Chemistry of Organic Natural Products; Herz, W.; Grisebach, H.; Kirby, G., Eds.; Springer-Verlag: Vienna, 1982; vol. 41, pp 206 - 340.
    • (1982) Progress in the Chemistry of Organic Natural Products , vol.41 , pp. 206-340
    • Daly, J.W.1
  • 4
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    • Brossi, A., Ed.; Academic Press: New York
    • (c) Witkop, B.; Gossinger, E. in The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; vol. 21, pp 139 - 251.
    • (1983) The Alkaloids , vol.21 , pp. 139-251
    • Witkop, B.1    Gossinger, E.2
  • 27
    • 0000997425 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford, However, the conformational and steric arguments we present relating to the structure shown in Fig. 1 should also apply to carbocationic intermediates
    • (c) As pointed out in refs. 8a, b, the type of reaction used in the present work is only formally an imino-ene reaction, and probably proceeds in astepwise fashion via cationic intermediates. See: Overman, L. E.; Ricca, D. in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; vol. 2, pp 1007 - 1046. However, the conformational and steric arguments we present relating to the structure shown in Fig. 1 should also apply to carbocationic intermediates.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1007-1046
    • Overman, L.E.1    Ricca, D.2
  • 30
    • 0010428453 scopus 로고    scopus 로고
    • note
    • 2 solution; two singlets observed for the racemate, only one for the resolved materials).
  • 36
    • 0010465802 scopus 로고
    • (d) Use of 1,3-dithiane itself under a variety of conditions [11e] gave at best 62% in the coupling reaction, but this was not reproducible. For other problems with the use of [2-(1,3-dithianyl)]lithium, see: Wade. P. A.; D'Ambrosio, S. G.; Murray, J. K., Jr. J. Org. Chem. 1995, 60, 4258.
    • (1995) J. Org. Chem. , vol.60 , pp. 4258
    • Wade, P.A.1    D'Ambrosio, S.G.2    Murray J.K., Jr.3
  • 37
    • 0001950161 scopus 로고    scopus 로고
    • and references therein
    • (e) For a recent discussion of 1,3-dithiane coupling as a key step in total synthesis, see: Smith, A. B., III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35 and references therein.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 35
    • Smith A.B. III1    Condon, S.M.2    McCauley, J.A.3
  • 40
    • 0010429452 scopus 로고    scopus 로고
    • note
    • 2 was tried and of the solvents tested, toluene/ether (1:1) proved to be best.
  • 44
    • 0010429310 scopus 로고    scopus 로고
    • note
    • 18. (a) For a similar procedure starting with the corresponding bromide, see réf. 16.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.