메뉴 건너뛰기




Volumn 64, Issue 8, 1999, Pages 2648-2656

Total synthesis of (-)-coriolin

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLYL COMPOUND; CORIOLIC ACID; EPOXIDE; HYDROXYL GROUP; NATURAL PRODUCT; SILANE DERIVATIVE; SILOXANE; SPIRO COMPOUND; SULFIDE; TRIACYLGLYCEROL LIPASE; VINYL DERIVATIVE;

EID: 0033574497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981478c     Document Type: Article
Times cited : (93)

References (61)
  • 6
    • 85083210739 scopus 로고
    • For reviews of cyclopentane synthesis, see: (a) Ramaiah, M. Synthesis 1984, 529.
    • (1984) Synthesis , pp. 529
    • Ramaiah, M.1
  • 8
    • 0001460582 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Chapter 3.1
    • For reviews of [3+2] cycloaddition reactions, see: (a) Little, R. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 3.1, pp 239-270.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 239-270
    • Little, R.D.1
  • 9
    • 0000384028 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Chapter 3.2
    • (b) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 3.2, pp 271-314.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 271-314
    • Chan, D.M.T.1
  • 11
    • 0032481619 scopus 로고    scopus 로고
    • (b) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 1724. Similar methylenecyclopentane annulation could also be effected by using the substrate having a TMS-methyl group in place of the siloxy group of 1b. Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943.
    • (1998) Am. Chem. Soc. , vol.120 , pp. 1724
    • Masuya, K.1    Domon, K.2    Tanino, K.3    Kuwajima, I.J.4
  • 12
    • 0030581417 scopus 로고    scopus 로고
    • (b) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 1724. Similar methylenecyclopentane annulation could also be effected by using the substrate having a TMS-methyl group in place of the siloxy group of 1b. Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5943
    • Takahashi, Y.1    Tanino, K.2    Kuwajima, I.3
  • 16
    • 0001674034 scopus 로고
    • Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K., Reissig, H.-U., Eds.; VCH: Weinheim
    • For a review of total synthesis of coriolin: Mulzer, J. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K., Reissig, H.-U., Eds.; VCH: Weinheim, 1991; pp 323-334.
    • (1991) Organic Synthesis Highlights , pp. 323-334
    • Mulzer, J.1
  • 17
    • 0022384411 scopus 로고
    • Fomal total synthesis of (±)-coriolin which were not covered in ref 6: (a) Hijfte, L. V.; Little, R. D. J. Org. Chem. 1985, 50, 3940.
    • (1985) J. Org. Chem. , vol.50 , pp. 3940
    • Hijfte, L.V.1    Little, R.D.2
  • 41
    • 0039960868 scopus 로고    scopus 로고
    • Hassner, A., Ed.; JAI Press: Greenwich, and references therein
    • For a recent review, see: Santaniello, E.; Ferraboschi, P. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, 1997; Vol. 2, pp 237-283, and references therein.
    • (1997) Advances in Asymmetric Synthesis , vol.2 , pp. 237-283
    • Santaniello, E.1    Ferraboschi, P.2
  • 43
    • 0344208244 scopus 로고    scopus 로고
    • Treatment of (S)-5 with N-p-toluenesulfonyl-L-phenylalaninyl chloride and pyridine afforded the corresponding ester, which was then converted into a sulfone derivative. See the Suporting Information
    • Treatment of (S)-5 with N-p-toluenesulfonyl-L-phenylalaninyl chloride and pyridine afforded the corresponding ester, which was then converted into a sulfone derivative. See the Suporting Information.
  • 44
    • 0345070406 scopus 로고    scopus 로고
    • note
    • 2 also failed to give enone 9, while 8 was slowly converted into 9 by heating at 180 °C.
  • 45
    • 0345501984 scopus 로고    scopus 로고
    • 4b See the Suporting information
    • 4b See the Suporting information.
  • 53
    • 0010578048 scopus 로고
    • and refs 7a,b,f, 9d, 10a-c
    • Enone 15 in racemic form: Koreeda, M.; Mislankar, S. G. J. Am. Chem. Soc. 1983, 105, 7203, and refs 7a,b,f, 9d, 10a-c.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7203
    • Koreeda, M.1    Mislankar, S.G.2
  • 55
    • 0345501982 scopus 로고    scopus 로고
    • note
    • 17 in the early stage of the total synthesis, and the rotation of (-)-coriolin was again confirmed at the last stage. We have also confirmed that compound 15 was obtained in optically pure form by our method (Suporting Information). Therefore, it seems that there are some errors in structual assignment made by Demuth, not only for 15 but also for 18.
  • 57
    • 0345501981 scopus 로고    scopus 로고
    • 26
    • 26
  • 59
    • 0000784042 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Chapter 1.13
    • Rosen, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, Chapter 1.13, pp 409-440.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 409-440
    • Rosen, T.1
  • 61
    • 0344208240 scopus 로고    scopus 로고
    • Use of potassium tert-butoxide resulted in a much more sluggish transformation
    • Use of potassium tert-butoxide resulted in a much more sluggish transformation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.