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Volumn 130, Issue 24, 2008, Pages 7568-7569

Total synthesis of (±)-actinophyllic acid

Author keywords

[No Author keywords available]

Indexed keywords

ACTINOPHYLLIC ACID; INDOLE ALKALOID; KETONE; MALONIC ACID DERIVATIVE; 2 N BUTYLMALONATE; 2-N-BUTYLMALONATE;

EID: 45249090324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803158y     Document Type: Article
Times cited : (113)

References (18)
  • 3
    • 0001626504 scopus 로고
    • For brief reviews, see: a
    • For brief reviews, see: (a) Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359.
    • (1992) Acc. Chem. Res , vol.25 , pp. 352-359
    • Overman, L.E.1
  • 9
    • 0000238887 scopus 로고
    • For the use of this oxidant in phenolic couplings, see: a
    • For the use of this oxidant in phenolic couplings, see: (a) Tobinaga, S.; Kotani, E. J. Am. Chem. Soc. 1972, 94, 309-310.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 309-310
    • Tobinaga, S.1    Kotani, E.2
  • 10
    • 0000867157 scopus 로고
    • In oxidative dimerization of ketones, see: b
    • In oxidative dimerization of ketones, see: (b) Frazier, R. H.; Harlow, R. L. J. Org. Chem. 1980, 45, 5408-5411.
    • (1980) J. Org. Chem , vol.45 , pp. 5408-5411
    • Frazier, R.H.1    Harlow, R.L.2
  • 11
    • 45249123334 scopus 로고    scopus 로고
    • This conversion was initially optimized with the dimethyl ester congener of 11. These studies showed that yields of the cyclized product were much lower using 2.0 equiv of LDA and 2.2 equiv of oxidant, or if Fe(acac) 3, FeCl3, Fe(cp)2PF6, or Cu(O 2CC5H11)2 was employed as the oxidant
    • 2 was employed as the oxidant.
  • 12
    • 0027260840 scopus 로고    scopus 로고
    • For examples of intramolecular oxidative coupling of two different ketone enolates, see: (a) Cohen, T, McNamara, K, Kuzemko, M. A, Ramig, K, Landi, J. J, Jr, Dong, Y. Tetrahedron 1993, 49, 7931-7942
    • For examples of intramolecular oxidative coupling of two different ketone enolates, see: (a) Cohen, T.; McNamara, K.; Kuzemko, M. A.; Ramig, K.; Landi, J. J., Jr.; Dong, Y. Tetrahedron 1993, 49, 7931-7942.
  • 16
    • 45249111660 scopus 로고    scopus 로고
    • The constitution and relative configuration of the α epimer was confirmed by single-crystal X-ray analysis
    • The constitution and relative configuration of the α epimer was confirmed by single-crystal X-ray analysis.
  • 18
    • 45249108554 scopus 로고    scopus 로고
    • Final purification of salt 17 by HPLC, as reported for the natural product,1 does not reproducibly give samples of 1 that show identical 1NMR spectra nor samples whose spectra precisely match those reported for natural 1 in DMSO-d6, we believe such samples are variable mixtures of zwitterionic 1 and salt 17. Addition of incremental amounts of sodium methylsulfinylmethylide-d 5 to hydrochloride salt 17 in DMSO-d6 revealed incremental shifts in most resonances. When ca. 1 equiv of base was added, a 1H NMR spectrum identical to that reported1 for natural 1 was obtained; see the Supporting Information for details. Unfortunately, a sample of natural actinophyllic acid is no longer available for direct comparison
    • 1 for natural 1 was obtained; see the Supporting Information for details. Unfortunately, a sample of natural actinophyllic acid is no longer available for direct comparison.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.