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Volumn 5, Issue 1, 1999, Pages 121-161

Asymmetric total synthesis of Taxol

Author keywords

Antitumor agents; Cyclizations; Natural products; Taxol; Total synthesis

Indexed keywords

TAXOL;

EID: 0032959568     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f     Document Type: Article
Times cited : (292)

References (126)
  • 4
    • 84943510383 scopus 로고
    • For reviews, see: b) C. S. Swindell, Org. Prep. Proced. Int. 1991, 23, 465; c) K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994, 33, 15.
    • (1991) Org. Prep. Proced. Int. , vol.23 , pp. 465
    • Swindell, C.S.1
  • 5
    • 0002767594 scopus 로고
    • For reviews, see: b) C. S. Swindell, Org. Prep. Proced. Int. 1991, 23, 465; c) K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994, 33, 15.
    • (1994) Angew. Chem. , vol.106 , pp. 38
    • Nicolaou, K.C.1    Dai, W.-M.2    Guy, R.K.3
  • 6
    • 0003185761 scopus 로고
    • For reviews, see: b) C. S. Swindell, Org. Prep. Proced. Int. 1991, 23, 465; c) K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994, 33, 15.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 15
  • 16
    • 33748237378 scopus 로고
    • a) J. J. Masters, J. T. Link, L. B. Snyder, W. B. Young, S. J. Danishefsky, Angew. Chem. 1995, 107, 1886; Angew. Chem. Int. Ed. Engl. 1995, 34, 1723;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1723
  • 21
    • 0029824092 scopus 로고    scopus 로고
    • and references therein
    • Prof. Isao Kuwajima presented the total synthesis of Taxol at the 7th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-7) on November 11th in 1997. See also total synthesis of (±)-taxusin: R. Hara, T. Furukawa, Y. Horiguchi, I. Kuwajima, J. Am. Chem. Soc. 1996, 118, 9186, and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9186
    • Hara, R.1    Furukawa, T.2    Horiguchi, Y.3    Kuwajima, I.4
  • 39
    • 0344692226 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-106693 (3), 106694 (56), and 111347 (82). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 50
    • 33751392448 scopus 로고
    • see also g) G. A. Molander, J. A. McKie, J. Org. Chem. 1992, 57, 3132; h) G. A. Molander, J. A. McKie, J. Org. Chem. 1994, 59, 3186; i) C. S. Swindell, W. Fan, J. Org. Chem. 1996, 61, 1109; j) C. S. Swindell, W. Fan, Tetrahedron Lett. 1996, 37, 2321.
    • (1992) J. Org. Chem. , vol.57 , pp. 3132
    • Molander, G.A.1    McKie, J.A.2
  • 51
    • 0000210522 scopus 로고
    • see also g) G. A. Molander, J. A. McKie, J. Org. Chem. 1992, 57, 3132; h) G. A. Molander, J. A. McKie, J. Org. Chem. 1994, 59, 3186; i) C. S. Swindell, W. Fan, J. Org. Chem. 1996, 61, 1109; j) C. S. Swindell, W. Fan, Tetrahedron Lett. 1996, 37, 2321.
    • (1994) J. Org. Chem. , vol.59 , pp. 3186
    • Molander, G.A.1    McKie, J.A.2
  • 52
    • 0030024340 scopus 로고    scopus 로고
    • see also g) G. A. Molander, J. A. McKie, J. Org. Chem. 1992, 57, 3132; h) G. A. Molander, J. A. McKie, J. Org. Chem. 1994, 59, 3186; i) C. S. Swindell, W. Fan, J. Org. Chem. 1996, 61, 1109; j) C. S. Swindell, W. Fan, Tetrahedron Lett. 1996, 37, 2321.
    • (1996) J. Org. Chem. , vol.61 , pp. 1109
    • Swindell, C.S.1    Fan, W.2
  • 53
    • 0029989538 scopus 로고    scopus 로고
    • see also g) G. A. Molander, J. A. McKie, J. Org. Chem. 1992, 57, 3132; h) G. A. Molander, J. A. McKie, J. Org. Chem. 1994, 59, 3186; i) C. S. Swindell, W. Fan, J. Org. Chem. 1996, 61, 1109; j) C. S. Swindell, W. Fan, Tetrahedron Lett. 1996, 37, 2321.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2321
    • Swindell, C.S.1    Fan, W.2
  • 60
    • 0344260534 scopus 로고    scopus 로고
    • All calculations were performed with the program package SPARTAN 5.0.3 (DEC version) of Wavefunction (18401 Von Karman Avenue, Suite 370 Irvine, CA 92612 (USA); http://www.wavefun.-com).
  • 63
    • 0002455223 scopus 로고
    • For reviews, see: a) W. P. Griffith, S. V. Ley, Aldrichimica Acta, 1990, 23, 13; b) S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis, 1994, 639.
    • (1990) Aldrichimica Acta , vol.23 , pp. 13
    • Griffith, W.P.1    Ley, S.V.2
  • 70
    • 0000811606 scopus 로고    scopus 로고
    • G. Stork, K. Manabe, L. Liu, J. Am. Chem. Soc. 1998, 120, 1337. Prof. Stork presented an AB to ABC ring-construction strategy by intramolecular aldol reaction in the Goto memorial lecture at Nagoya University on April 28th, 1995.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1337
    • Stork, G.1    Manabe, K.2    Liu, L.3
  • 73
    • 85083243520 scopus 로고
    • For a review, see: J. Tsuji, Synthesis, 1984, 369.
    • (1984) Synthesis , pp. 369
    • Tsuji, J.1
  • 78
    • 4243973410 scopus 로고
    • For reviews, see: e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) D. Lenoir, Synthesis, 1989, 883; g) A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1989) Chem. Rev. , vol.89 , pp. 1513
    • McMurry, J.E.1
  • 79
    • 0024784582 scopus 로고
    • For reviews, see: e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) D. Lenoir, Synthesis, 1989, 883; g) A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1989) Synthesis , pp. 883
    • Lenoir, D.1
  • 80
    • 0001359722 scopus 로고    scopus 로고
    • For reviews, see: e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) D. Lenoir, Synthesis, 1989, 883; g) A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1996) Angew. Chem. , vol.108 , pp. 2582
    • Fürstner, A.1    Bogdanovic, B.2
  • 81
    • 0030444646 scopus 로고    scopus 로고
    • For reviews, see: e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) D. Lenoir, Synthesis, 1989, 883; g) A. Fürstner, B. Bogdanovic, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2442
  • 82
    • 0009540557 scopus 로고
    • 3 by a literature method: a) R. C. Paul, A. Arneja, S. P. Narula, Inorg. Nucl. Chem. Lett. 1969, 5, 1013; b) S. P. Narula, H. K. Sharma, Inorg. Synth. 1986, 24, 181. See also: c) T. Mukaiyama, A. Kagayama, I. Shiina, Chem. Lett. 1998, 1107.
    • (1969) Inorg. Nucl. Chem. Lett. , vol.5 , pp. 1013
    • Paul, R.C.1    Arneja, A.2    Narula, S.P.3
  • 83
    • 0000886849 scopus 로고
    • 3 by a literature method: a) R. C. Paul, A. Arneja, S. P. Narula, Inorg. Nucl. Chem. Lett. 1969, 5, 1013; b) S. P. Narula, H. K. Sharma, Inorg. Synth. 1986, 24, 181. See also: c) T. Mukaiyama, A. Kagayama, I. Shiina, Chem. Lett. 1998, 1107.
    • (1986) Inorg. Synth. , vol.24 , pp. 181
    • Narula, S.P.1    Sharma, H.K.2
  • 84
    • 0032265034 scopus 로고    scopus 로고
    • 3 by a literature method: a) R. C. Paul, A. Arneja, S. P. Narula, Inorg. Nucl. Chem. Lett. 1969, 5, 1013; b) S. P. Narula, H. K. Sharma, Inorg. Synth. 1986, 24, 181. See also: c) T. Mukaiyama, A. Kagayama, I. Shiina, Chem. Lett. 1998, 1107.
    • (1998) Chem. Lett. , pp. 1107
    • Mukaiyama, T.1    Kagayama, A.2    Shiina, I.3
  • 86
    • 0000146469 scopus 로고
    • For a review, see: E. Block, Org. React. 1984, 30, 457.
    • (1984) Org. React. , vol.30 , pp. 457
    • Block, E.1
  • 100
    • 3743147656 scopus 로고
    • Eur. Pat. Appl. EP 400971, 1990
    • a) R. A. Holton, Eur. Pat. Appl. EP 400971, 1990 [Chem. Abstr. 1991, 114, 164568q];
    • (1991) Chem. Abstr. , vol.114
    • Holton, R.A.1
  • 108
    • 0029742395 scopus 로고    scopus 로고
    • a) C. Gennari, A. Vulpetti, M. Donghi, N. Mongelli, E. Vanotti, Angew. Chem. 1996, 108, 1809; Angew. Chem. Int. Ed. Engl. 1996, 35, 1723;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1723
  • 121
    • 84985580791 scopus 로고
    • b) M. T. Reetz, K. Kesseler, A. Jung, Angew. Chem. 1985, 97, 989; Angew. Chem. Int. Ed. Engl. 1985, 24, 989.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 989


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.