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Volumn 43, Issue 43, 2002, Pages 7831-7834

Enantioselective synthesis of the C11-C17 segment of soraphen A1α via organoiron methodology

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; GLYCERALDEHYDE; SORAPHEN A; UNCLASSIFIED DRUG;

EID: 0037152307     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01727-6     Document Type: Article
Times cited : (9)

References (26)
  • 6
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    • For other examples of 1,6-asymmetric control using (diene)iron complexes, see: (a) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151-2152; (b) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656. For examples of 1,8- and 1,10-asymmetric induction using (diene)iron complexes, see: © Takemoto, Y.; Ishii, K.; Honda, A.; Okamoto, K.; Yanada, R.; Ibuka, T. Chem. Commun. 2000, 1445-1446; (d) Takemoto, Y.; Ishii, K.; Ibuka, T.; Miwa, Y.; Taga, T.; Nakao, S.; Tanaka, T.; Ohishi, H.; Kai, Y.; Kanehisa, N. J. Org. Chem. 2001, 66, 6116-6123.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2151-2152
    • Roush, W.R.1    Wada, C.K.2
  • 7
    • 0034612132 scopus 로고    scopus 로고
    • For other examples of 1,6-asymmetric control using (diene)iron complexes, see: (a) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151-2152; (b) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656. For examples of 1,8- and 1,10-asymmetric induction using (diene)iron complexes, see: © Takemoto, Y.; Ishii, K.; Honda, A.; Okamoto, K.; Yanada, R.; Ibuka, T. Chem. Commun. 2000, 1445-1446; (d) Takemoto, Y.; Ishii, K.; Ibuka, T.; Miwa, Y.; Taga, T.; Nakao, S.; Tanaka, T.; Ohishi, H.; Kai, Y.; Kanehisa, N. J. Org. Chem. 2001, 66, 6116-6123.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3653-3656
    • Takemoto, Y.1    Baba, Y.2    Saha, G.3    Nakao, S.4    Iwata, C.5    Tanaka, T.6    Ibuka, T.7
  • 8
    • 0034617932 scopus 로고    scopus 로고
    • For other examples of 1,6-asymmetric control using (diene)iron complexes, see: (a) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151-2152; (b) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656. For examples of 1,8- and 1,10-asymmetric induction using (diene)iron complexes, see: © Takemoto, Y.; Ishii, K.; Honda, A.; Okamoto, K.; Yanada, R.; Ibuka, T. Chem. Commun. 2000, 1445-1446; (d) Takemoto, Y.; Ishii, K.; Ibuka, T.; Miwa, Y.; Taga, T.; Nakao, S.; Tanaka, T.; Ohishi, H.; Kai, Y.; Kanehisa, N. J. Org. Chem. 2001, 66, 6116-6123.
    • (2000) Chem. Commun. , pp. 1445-1446
    • Takemoto, Y.1    Ishii, K.2    Honda, A.3    Okamoto, K.4    Yanada, R.5    Ibuka, T.6
  • 9
    • 0035823167 scopus 로고    scopus 로고
    • For other examples of 1,6-asymmetric control using (diene)iron complexes, see: (a) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151-2152; (b) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656. For examples of 1,8- and 1,10-asymmetric induction using (diene)iron complexes, see: © Takemoto, Y.; Ishii, K.; Honda, A.; Okamoto, K.; Yanada, R.; Ibuka, T. Chem. Commun. 2000, 1445-1446; (d) Takemoto, Y.; Ishii, K.; Ibuka, T.; Miwa, Y.; Taga, T.; Nakao, S.; Tanaka, T.; Ohishi, H.; Kai, Y.; Kanehisa, N. J. Org. Chem. 2001, 66, 6116-6123.
    • (2001) J. Org. Chem. , vol.66 , pp. 6116-6123
    • Takemoto, Y.1    Ishii, K.2    Ibuka, T.3    Miwa, Y.4    Taga, T.5    Nakao, S.6    Tanaka, T.7    Ohishi, H.8    Kai, Y.9    Kanehisa, N.10
  • 16
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    • A similar intramolecular attack of alcoholate anion on iron has been proposed to account for the lack of reactivity of complexes chlorohydrins under basic conditions and for an unusual epimerization. See: (a) Lellouche, J. P.; Bulot, E.; Beaucourt, J. P.; Martelli, J.; Grée, R. J. Organomet. Chem. 1988, 342, C21-C23; (b) Lellouche, J.-P.; Gigou-Barbedette, A.; Grée, R. J. Organomet. Chem. 1993, 461, 167-168.
    • (1988) J. Organomet. Chem. , vol.342 , pp. C21-C23
    • Lellouche, J.P.1    Bulot, E.2    Beaucourt, J.P.3    Martelli, J.4    Grée, R.5
  • 17
    • 0010648145 scopus 로고
    • A similar intramolecular attack of alcoholate anion on iron has been proposed to account for the lack of reactivity of complexes chlorohydrins under basic conditions and for an unusual epimerization. See: (a) Lellouche, J. P.; Bulot, E.; Beaucourt, J. P.; Martelli, J.; Grée, R. J. Organomet. Chem. 1988, 342, C21-C23; (b) Lellouche, J.-P.; Gigou-Barbedette, A.; Grée, R. J. Organomet. Chem. 1993, 461, 167-168.
    • (1993) J. Organomet. Chem. , vol.461 , pp. 167-168
    • Lellouche, J.-P.1    Gigou-Barbedette, A.2    Grée, R.3
  • 21
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    • 4 on diastereoselectivity of nucleophilic attack, see: Harvey D.F., Selchau V.B. J. Org. Chem. 65:2000;2282-2286.
    • (2000) J. Org. Chem. , vol.65 , pp. 2282-2286
    • Harvey, D.F.1    Selchau, V.B.2
  • 22
    • 84992240794 scopus 로고    scopus 로고
    • 3): δ 7.28-7.15 (m, 5H), 5.25 (m, 2H), 4.51 (br d, J=7.9 Hz, 1H), 3.61 (dd, J=3.7, 11.0 Hz, 1H), 3.59 (dd, J=5.8, 11.0 Hz, 1H), 3.38 (s, 3H), 3.04 (m, 1H), 1.85 (br s, OH), 1.22 (m, 1H), 0.88 (m and s, 10H), 0.05 (s, 6H)
    • 3): δ 7.28-7.15 (m, 5H), 5.25 (m, 2H), 4.51 (br d, J=7.9 Hz, 1H), 3.61 (dd, J=3.7, 11.0 Hz, 1H), 3.59 (dd, J=5.8, 11.0 Hz, 1H), 3.38 (s, 3H), 3.04 (m, 1H), 1.85 (br s, OH), 1.22 (m, 1H), 0.88 (m and s, 10H), 0.05 (s, 6H).
  • 25
    • 84992240799 scopus 로고    scopus 로고
    • 3): δ 7.37-7.20 (m, 5H), 5.25 (m, 2H), 4.51 (br d, J=7.2 Hz, 1H), 3.67 (dd, J=6.6, 10.5 Hz, 1H), 3.47 (s and m, 4H), 3.20 (m, 1H), 1.84 (br s, OH), 1.20 (m, 1H), 0.89 (m and s, 9H), 0.05 (s, 6H)
    • 3): δ 7.37-7.20 (m, 5H), 5.25 (m, 2H), 4.51 (br d, J=7.2 Hz, 1H), 3.67 (dd, J=6.6, 10.5 Hz, 1H), 3.47 (s and m, 4H), 3.20 (m, 1H), 1.84 (br s, OH), 1.20 (m, 1H), 0.89 (m and s, 9H), 0.05 (s, 6H).
  • 26
    • 84992260797 scopus 로고    scopus 로고
    • 3): δ 143.4, 136.1, 132.9, 132.6, 130.6, 129.2, 128.4, 126.9, 83.5, 75.4, 66.9, 57.6, 26.6, 19.1, -4.5
    • 3): δ 143.4, 136.1, 132.9, 132.6, 130.6, 129.2, 128.4, 126.9, 83.5, 75.4, 66.9, 57.6, 26.6, 19.1, -4.5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.