메뉴 건너뛰기




Volumn 55, Issue 33, 1999, Pages 10087-10100

An improved preparation of the desmethyl qinghao acid precursor of (±)- 6,9-desmethylqinghaosu

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALUMINUM DERIVATIVE; ARTEMISIN DERIVATIVE; ARTEMISINIC ACID; CHLORIDE; ETHER DERIVATIVE; KETONE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

EID: 0033551709     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00543-8     Document Type: Article
Times cited : (3)

References (30)
  • 1
    • 44949278235 scopus 로고
    • For reviews see: Zaman, S. S.; Sharma, R. P. Heterocycles 1991, 32, 1593; Zhou, W. S. Acc. Chem. Res. 1994, 27, 211.
    • (1991) Heterocycles , vol.32 , pp. 1593
    • Zaman, S.S.1    Sharma, R.P.2
  • 2
    • 0001985625 scopus 로고
    • For reviews see: Zaman, S. S.; Sharma, R. P. Heterocycles 1991, 32, 1593; Zhou, W. S. Acc. Chem. Res. 1994, 27, 211.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 211
    • Zhou, W.S.1
  • 3
    • 0020577131 scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 624
    • Schmid, G.1    Hofheinz, W.2
  • 4
    • 0026584198 scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 974
    • Avery, M.A.1    Chong, W.K.M.2    Jennings-White, C.3
  • 5
    • 0027291372 scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4435
    • Liu, H.J.1    Yeh, W.L.2    Chew, S.Y.3
  • 6
    • 0009644257 scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1986) Tetrahedron , vol.42 , pp. 819
    • Zhou, W.S.1    Zhu, J.2    Huang, D.Z.3    Zhou, W.S.4
  • 7
    • 0025171976 scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 755
    • Ravindranathan, T.1    Kumar, M.A.2    Menon, R.B.3    Hiremath, S.V.4
  • 8
    • 0030068917 scopus 로고    scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1996) Syn. Commun. , vol.26 , pp. 321
    • Constantino, M.G.1    Beltrame, M.2    Da Silva, G.V.J.3
  • 9
    • 0023555566 scopus 로고
    • Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624; Avery, M. A.; Chong, W. K. M.; Jennings-White, C. J. Am. Chem. Soc. 1992, 114, 974; Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett. 1993, 34, 4435; Zhou, W. S.; Zhu, J.; Huang, D. Z.; Zhou, W. S. Tetrahedron 1986, 42, 819; Ravindranathan, T.; Kumar, M. A.; Menon, R. B.; Hiremath, S. V. Tetrahedron Lett. 1990, 31, 755; Constantino, M. G.; Beltrame, M..; da Silva, G. V. J. Syn. Commun. 1996, 26, 321; Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4629
    • Avery, M.A.1    Jennings-White, C.2    Chong, W.K.M.3
  • 10
    • 0001029321 scopus 로고
    • Deng, D.; Zhu, D.; Gao, Y.; Dai, J.; Xu, R. Kexue Tongbao, 1982, 27, 1359; Klayman, D. L.; Lin, A. J.; Acton, N.; Scovill, J. P.; Hoch, J. M.; Milhous, W. K.; Theoharides, A. D.; Dobek, A. S. J. Nat. Prod. 1984, 47, 715-717.
    • (1982) Kexue Tongbao , vol.27 , pp. 1359
    • Deng, D.1    Zhu, D.2    Gao, Y.3    Dai, J.4    Xu, R.5
  • 12
    • 0024429567 scopus 로고
    • Roth, R. J.; Acton, N. J. Nat. Prod. 1989, 52, 1183; Roth, R. J.; Acton, N. J. Chem. Ed. 1991, 68, 612.
    • (1989) J. Nat. Prod. , vol.52 , pp. 1183
    • Roth, R.J.1    Acton, N.2
  • 13
    • 0000044579 scopus 로고
    • Roth, R. J.; Acton, N. J. Nat. Prod. 1989, 52, 1183; Roth, R. J.; Acton, N. J. Chem. Ed. 1991, 68, 612.
    • (1991) J. Chem. Ed. , vol.68 , pp. 612
    • Roth, R.J.1    Acton, N.2
  • 14
    • 0009644258 scopus 로고    scopus 로고
    • Provisional Patent P6989, September 1989
    • Haynes, R. K.; Vonwiller, S. C. Provisional Patent P6989, September 1989; Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc. Chem. Commun. 1990, 451; Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc. Chem. Commun. 1990, 449.
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 15
    • 0025269828 scopus 로고
    • Haynes, R. K.; Vonwiller, S. C. Provisional Patent P6989, September 1989; Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc. Chem. Commun. 1990, 451; Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc. Chem. Commun. 1990, 449.
    • (1990) J. Chem. Soc. Chem. Commun. , pp. 451
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 16
    • 37049080191 scopus 로고
    • Haynes, R. K.; Vonwiller, S. C. Provisional Patent P6989, September 1989; Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc. Chem. Commun. 1990, 451; Haynes, R. K.; Vonwiller, S. C. J. Chem. Soc. Chem. Commun. 1990, 449.
    • (1990) J. Chem. Soc. Chem. Commun. , pp. 449
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 18
    • 4243380693 scopus 로고
    • Int. Applic. PCT/AU90/00456 (27/9/90) WO
    • Haynes, R. K.; Vonwiller, S. C. Int. Applic. PCT/AU90/00456 (27/9/90) WO (Chem. Abs. 1992, 116, 59094a); Haynes, R. K.; Vonwiller, S. C. Synlett 1992, 481; Haynes, R. K.; Vonwiller, S. C. PCT Int. Applic. WO 920195 (29/4/93) (Chem. Abs. 1993, 119, 181047q); Haynes, R. K.; Vonwiller, S. C.; Wang, H. -J. Tetrahedron Lett. 1995, 36, 4641.
    • (1992) Chem. Abs. , vol.116
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 19
    • 84928945683 scopus 로고
    • Haynes, R. K.; Vonwiller, S. C. Int. Applic. PCT/AU90/00456 (27/9/90) WO (Chem. Abs. 1992, 116, 59094a); Haynes, R. K.; Vonwiller, S. C. Synlett 1992, 481; Haynes, R. K.; Vonwiller, S. C. PCT Int. Applic. WO 920195 (29/4/93) (Chem. Abs. 1993, 119, 181047q); Haynes, R. K.; Vonwiller, S. C.; Wang, H. -J. Tetrahedron Lett. 1995, 36, 4641.
    • (1992) Synlett , pp. 481
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 20
    • 4243390801 scopus 로고
    • PCT Int. Applic. WO 920195 (29/4/93)
    • Haynes, R. K.; Vonwiller, S. C. Int. Applic. PCT/AU90/00456 (27/9/90) WO (Chem. Abs. 1992, 116, 59094a); Haynes, R. K.; Vonwiller, S. C. Synlett 1992, 481; Haynes, R. K.; Vonwiller, S. C. PCT Int. Applic. WO 920195 (29/4/93) (Chem. Abs. 1993, 119, 181047q); Haynes, R. K.; Vonwiller, S. C.; Wang, H. -J. Tetrahedron Lett. 1995, 36, 4641.
    • (1993) Chem. Abs. , vol.119
    • Haynes, R.K.1    Vonwiller, S.C.2
  • 21
    • 0029062757 scopus 로고
    • Haynes, R. K.; Vonwiller, S. C. Int. Applic. PCT/AU90/00456 (27/9/90) WO (Chem. Abs. 1992, 116, 59094a); Haynes, R. K.; Vonwiller, S. C. Synlett 1992, 481; Haynes, R. K.; Vonwiller, S. C. PCT Int. Applic. WO 920195 (29/4/93) (Chem. Abs. 1993, 119, 181047q); Haynes, R. K.; Vonwiller, S. C.; Wang, H. -J. Tetrahedron Lett. 1995, 36, 4641.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4641
    • Haynes, R.K.1    Vonwiller, S.C.2    Wang, H.-J.3
  • 22
    • 0024453132 scopus 로고
    • Whilst this work is related to, and appears to be contemporaneous with, that of Acton (ref. 4), and of Haynes and Vonwiller (ref. 5), Jung seems not to have appreciated the nature of the oxygenation- cyclization (see Scheme 1 in the Jung paper, cf. Jung's structure 8 for which no data is presented)
    • Jung, M.; Li, X.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Tetrahedron Lett. 1989, 30, 5973. Whilst this work is related to, and appears to be contemporaneous with, that of Acton (ref. 4), and of Haynes and Vonwiller (ref. 5), Jung seems not to have appreciated the nature of the oxygenation- cyclization (see Scheme 1 in the Jung paper, cf. Jung's structure 8 for which no data is presented).
    • (1989) Tetrahedron Lett. , vol.30 , pp. 5973
    • Jung, M.1    Li, X.2    Bustos, D.A.3    ElSohly, H.N.4    McChesney, J.D.5
  • 23
    • 0009610845 scopus 로고
    • Bustos, D. A.; Jung, M.; ElSohly, H. N.; McChesney, J. D. Heterocycles 1989, 29, 2773; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1990, 743. Jung, M.; Yu, D.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Bioorganic Med. Chem. Lett. 1991, 1, 741; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1993, 43.
    • (1989) Heterocycles , vol.29 , pp. 2773
    • Bustos, D.A.1    Jung, M.2    ElSohly, H.N.3    McChesney, J.D.4
  • 24
    • 84892189202 scopus 로고
    • Bustos, D. A.; Jung, M.; ElSohly, H. N.; McChesney, J. D. Heterocycles 1989, 29, 2773; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1990, 743. Jung, M.; Yu, D.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Bioorganic Med. Chem. Lett. 1991, 1, 741; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1993, 43.
    • (1990) Synlett , pp. 743
    • Jung, M.1    Bustos, D.A.2    ElSohly, H.N.3    McChesney, J.D.4
  • 25
    • 0026345770 scopus 로고
    • Bustos, D. A.; Jung, M.; ElSohly, H. N.; McChesney, J. D. Heterocycles 1989, 29, 2773; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1990, 743. Jung, M.; Yu, D.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Bioorganic Med. Chem. Lett. 1991, 1, 741; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1993, 43.
    • (1991) Bioorganic Med. Chem. Lett. , vol.1 , pp. 741
    • Jung, M.1    Yu, D.2    Bustos, D.A.3    ElSohly, H.N.4    McChesney, J.D.5
  • 26
    • 0009626370 scopus 로고
    • Bustos, D. A.; Jung, M.; ElSohly, H. N.; McChesney, J. D. Heterocycles 1989, 29, 2773; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1990, 743. Jung, M.; Yu, D.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Bioorganic Med. Chem. Lett. 1991, 1, 741; Jung, M.; Bustos, D. A.; ElSohly, H. N.; McChesney, J. D. Synlett 1993, 43.
    • (1993) Synlett , pp. 43
    • Jung, M.1    Bustos, D.A.2    ElSohly, H.N.3    McChesney, J.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.