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Volumn 61, Issue 26, 1996, Pages 9560-9563

Efficient synthesis of 1-aryl-3,4-dihydro-4-hydroxynaphthalene: Application to the stereocontrolled synthesis of (±)-isopicropodophyllin and (±)-isopodophyllotoxin

Author keywords

[No Author keywords available]

Indexed keywords

ISOPICROPODOPHYLLIN; ISOPODOPHYLLOTOXIN; PODOPHYLLOTOXIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030446167     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609384     Document Type: Article
Times cited : (16)

References (34)
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    • (1990) Lignans
    • Ayres, D.C.1    Loike, J.D.2
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    • (d) Ogiku, T; Yoshida, S.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Synlett 1992, 651. For a recent review for the synthesis of podophyllotoxin and related compounds, see Ward, R. S. Synthesis 1992, 719.
    • (1992) Synthesis , pp. 719
    • Ward, R.S.1
  • 13
    • 37049080770 scopus 로고
    • Recently, we have reported the synthesis of heteroaromatic arylnaphthalene lignans from acetoxyaldehydes via heteroaromatic arylisobenzofurans. Kuroda, T.; Takahashi, M.; Ogiku, T.; Ohmizu, H.; Kondo, K.; Iwasaki, T. J. Chem. Soc., Chem. Commun. 1991, 1635. Kuroda, T.; Takahashi, M.; Ogiku, T.; Ohmizu, H.; Nishitani, T.; Kondo, K.; Iwasaki, T. J. Org. Chem. 1994, 59, 7353.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1635
    • Kuroda, T.1    Takahashi, M.2    Ogiku, T.3    Ohmizu, H.4    Kondo, K.5    Iwasaki, T.6
  • 14
    • 33751158229 scopus 로고
    • Recently, we have reported the synthesis of heteroaromatic arylnaphthalene lignans from acetoxyaldehydes via heteroaromatic arylisobenzofurans. Kuroda, T.; Takahashi, M.; Ogiku, T.; Ohmizu, H.; Kondo, K.; Iwasaki, T. J. Chem. Soc., Chem. Commun. 1991, 1635. Kuroda, T.; Takahashi, M.; Ogiku, T.; Ohmizu, H.; Nishitani, T.; Kondo, K.; Iwasaki, T. J. Org. Chem. 1994, 59, 7353.
    • (1994) J. Org. Chem. , vol.59 , pp. 7353
    • Kuroda, T.1    Takahashi, M.2    Ogiku, T.3    Ohmizu, H.4    Nishitani, T.5    Kondo, K.6    Iwasaki, T.7
  • 17
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    • note
    • The use of p-toluenesulfonic acid in lieu of TFA caused a considerable decrease in yield of 11 (38%) with concomitant formation of 12 (9%).
  • 18
    • 0003467672 scopus 로고
    • Wiley-Interscience: New York
    • The formation of 11 rather than the 1-hydroxy compound A can be attributed to the greater stability of the transient diaryl carbocation B compared to the monoaryl one C. See, for example : March, J. Advanced Organic Chemistry, 4th ed.; Wiley-Interscience: New York, 1992; pp 165-174.
    • (1992) Advanced Organic Chemistry, 4th Ed. , pp. 165-174
    • March, J.1
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    • (e) For the hydroxyl-directed hydrogenation using metal hydrides, see: Iio, H.; Isobe, M.; Kawai, T.; Goto, T. J. Am. Chem. Soc. 1979, 101, 6076. Salomon, R. G.; Sachinvala, N. D.; Raychaudhuri, S. R.; Miller, D. B. J. Am. Chem. Soc. 1984, 106, 2211. Hanzawa, Y.; Kawagoe, K.; Kawada, K.; Kobayashi, Y. Chem. Pharm. Bull. 1985, 33, 2579.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6076
    • Iio, H.1    Isobe, M.2    Kawai, T.3    Goto, T.4
  • 25
    • 0000709995 scopus 로고
    • (e) For the hydroxyl-directed hydrogenation using metal hydrides, see: Iio, H.; Isobe, M.; Kawai, T.; Goto, T. J. Am. Chem. Soc. 1979, 101, 6076. Salomon, R. G.; Sachinvala, N. D.; Raychaudhuri, S. R.; Miller, D. B. J. Am. Chem. Soc. 1984, 106, 2211. Hanzawa, Y.; Kawagoe, K.; Kawada, K.; Kobayashi, Y. Chem. Pharm. Bull. 1985, 33, 2579.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 2211
    • Salomon, R.G.1    Sachinvala, N.D.2    Raychaudhuri, S.R.3    Miller, D.B.4
  • 26
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    • (e) For the hydroxyl-directed hydrogenation using metal hydrides, see: Iio, H.; Isobe, M.; Kawai, T.; Goto, T. J. Am. Chem. Soc. 1979, 101, 6076. Salomon, R. G.; Sachinvala, N. D.; Raychaudhuri, S. R.; Miller, D. B. J. Am. Chem. Soc. 1984, 106, 2211. Hanzawa, Y.; Kawagoe, K.; Kawada, K.; Kobayashi, Y. Chem. Pharm. Bull. 1985, 33, 2579.
    • (1985) Chem. Pharm. Bull. , vol.33 , pp. 2579
    • Hanzawa, Y.1    Kawagoe, K.2    Kawada, K.3    Kobayashi, Y.4
  • 27
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    • note
    • 3,13,14
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    • note
    • 4, see ref 11a-c.
  • 34
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    • note
    • 3 have previously been reported.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.