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Volumn , Issue 15, 2008, Pages 2323-2326

A concise enantioselective strategy to (+)-(R)-goniothalamin and (+)-(R)-goniothalamin oxide by employing hydrolytic kinetic resolution and ring-closing metathesis as key steps

Author keywords

Goniothalamin; Jacobsen's epoxidation; Metathesis; Natural products; Styryl lactones

Indexed keywords

BIOLOGICAL ACTIVITIES; DIASTEREOMERIC EXCESS; ENANTIOSELECTIVE; GONIOTHALAMIN; HIGH YIELD; HYDROLYTIC KINETIC RESOLUTION; JACOBSEN'S EPOXIDATION; METATHESIS; NATURAL PRODUCTS; RING-CLOSING METATHESIS; STYRYL LACTONES;

EID: 49649123062     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067175     Document Type: Article
Times cited : (17)

References (58)
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    • 0021979081 scopus 로고    scopus 로고
    • Goniothalamin was also isolated from: (a) Goniothalamus giganteus: El-Zayat, A. E.; Ferrigni, N. R.; McCloud, T. G.; Mckenzie, A. T.; Byrn, S. R.; Cassady, J. M.; Chang, C.; McLuglin, J. L. Tetrahedron Lett. 1985, 26, 955.
    • Goniothalamin was also isolated from: (a) Goniothalamus giganteus: El-Zayat, A. E.; Ferrigni, N. R.; McCloud, T. G.; Mckenzie, A. T.; Byrn, S. R.; Cassady, J. M.; Chang, C.; McLuglin, J. L. Tetrahedron Lett. 1985, 26, 955.
  • 15
    • 0000367821 scopus 로고    scopus 로고
    • Goniothalamus uvaroids: Ahmad, F. B.; Tukol, W. A.; Omar, S.; Sharif, A. M. Phytochemistry 1991, 30, 2430.
    • (b) Goniothalamus uvaroids: Ahmad, F. B.; Tukol, W. A.; Omar, S.; Sharif, A. M. Phytochemistry 1991, 30, 2430.
  • 16
    • 49649117828 scopus 로고    scopus 로고
    • Goniothalamus malayanus, G. andersonni, G. macrophyllus, and G. velutinus: Jewers, K.; Blunden, G.; Wetchapinan, S.; Dougan, J.; Manchada, A. H.; Davis, J. B.; Kyi, A. Phytochemistry 1972, 11, 2025.
    • (c) Goniothalamus malayanus, G. andersonni, G. macrophyllus, and G. velutinus: Jewers, K.; Blunden, G.; Wetchapinan, S.; Dougan, J.; Manchada, A. H.; Davis, J. B.; Kyi, A. Phytochemistry 1972, 11, 2025.
  • 17
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    • Goniothalamus dolichocarpus: Goh, S. H.; Ee, G. C. L.; Chuah, C. H.; Wei, C. Aust. J. Chem. 1995, 48, 199.
    • (d) Goniothalamus dolichocarpus: Goh, S. H.; Ee, G. C. L.; Chuah, C. H.; Wei, C. Aust. J. Chem. 1995, 48, 199.
  • 18
    • 49649100307 scopus 로고    scopus 로고
    • Some of the species are widely used as traditional medicines. See: (a) Kan, W. S. Pharmaceutical Botany; National Research Institute of Chinese Medicine: Taipei, 1979, 247.
    • Some of the species are widely used as traditional medicines. See: (a) Kan, W. S. Pharmaceutical Botany; National Research Institute of Chinese Medicine: Taipei, 1979, 247.
  • 31
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    • Selected examples: (a) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201.
    • Selected examples: (a) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201.
  • 45
    • 0032580376 scopus 로고    scopus 로고
    • For an excellent recent review, see: a
    • For an excellent recent review, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 53
    • 49649107884 scopus 로고    scopus 로고
    • R)-Goniothalamin (1, White crystalline solid; mp 82-83°C (Lit.161 81-82°C, α]D +169.4 (c 1.45, CHCl3, Lit.6 [α]D +170.3 (c 1.38, CHCl3, IR (KBr, 3050, 3025, 2931, 1722, 1610, 1245, 810, 700 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.55 (m, 2 H, 5.12 (dq, J5,6, 6.5 Hz, J5,4, 1.2 Hz, 1 H, 6.11 (dt, J2,3, 9.7 Hz, J2,4, 1.7 Hz, 1 H, 6.29 (dd, J6,7, 16.1 Hz, J6,5, 6.5Hz, 1 H, 6.74 (d, J7,6, 15.6 Hz, 1 H, 6.94 (dt, J3,2, 9.7 Hz, J3,4, 4.4 Hz, 1 H, 7.30-7.42 (m, 5 H, 13C NMR (75 MHz, CDCl3, δ, 30.1, 77.9, 121.8, 125.5, 126.7, 128.4, 133.3, 135.2, 144.8, 164.1. MS(APCI, m/z, 201.0 (39, M, H, 183.1 (100, 155.2 66, 130
    • + + H], 183.1 (100), 155.2 (66), 130.1 (41).
  • 56
    • 33745738416 scopus 로고    scopus 로고
    • Work on a similar line has been reported: Pospisil, J.; Marko, I. E. Tetrahedron Lett. 2006, 47, 5933.
    • Work on a similar line has been reported: Pospisil, J.; Marko, I. E. Tetrahedron Lett. 2006, 47, 5933.
  • 58
    • 49649115997 scopus 로고    scopus 로고
    • R)-Goniothalamin Oxide (2, Mp 90-92°C (Lit. 25b 90-94°C, α]D +100.1 (c 0.88, CHCl3, Lit.25b [α]D +100.7 (c 0.70, CHCl3, IR (KBr, 3055, 3025, 2928, 1720, 1605, 1245, 1035, 808 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.59 (m, 2 H, 3.28 (dd, J6,5, 5.6 Hz, J6,7, 2.0 Hz, 1 H, 3.91 (d, J7,6, 1.8 Hz, 1 H, 4.45 (dt, J5,4, 9.4 Hz, J5,4¢ and 6, 5.5 Hz, 1 H, 6.07 (dt, J2,3, 9.7 Hz, J2,4, 2.0 Hz, 1 H, 6.95 (m, 1 H, 7.32-7.39 (m, 5 H, 13C NMR (75 MHz, CDCl 3, δ, 26.3, 57.5, 61.9, 77.2, 121.6, 125.5, 128.7, 135.5, 144.4, 164.0. MS (APCI, m/z, 217.0 (100, M, H, 199.0 (45, 171.1 (83, 143.1 (45, 139.0 (32, 105.0 (31, 91.0 31, HRMS: m/z
    • 3: 239.0684; found: 239.0682.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.