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Volumn 9, Issue 13, 2007, Pages 2585-2588

Total synthesis of amphidinolide y by formation of trisubstituted (E)-double bond via ring-closing metathesis of densely functionalized alkenes

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EID: 34547173573     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0710360     Document Type: Article
Times cited : (69)

References (59)
  • 1
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    • For reviews, see: a
    • For reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
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  • 8
    • 1442360753 scopus 로고    scopus 로고
    • Grubbs, R. H, Ed, Wiley-VCH: Weinheim, Germany, Vols
    • Also see: Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany. 2003: Vols. 1, 2, 3.
    • (2003) Handbook of Metathesis , vol.1 and 2and 3
  • 13
    • 33746066374 scopus 로고    scopus 로고
    • For the first total synthesis of amphidinolide Y, see
    • For the first total synthesis of amphidinolide Y, see: Fürstner, A.; Kattnig, E.; Lepage, O. J. Am. Chem. Soc. 2006, 128, 9194-9204.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 9194-9204
    • Fürstner, A.1    Kattnig, E.2    Lepage, O.3
  • 15
    • 10344255694 scopus 로고    scopus 로고
    • For the first total synthesis of amphidinolide X, see
    • For the first total synthesis of amphidinolide X, see: Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970-15971.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 15970-15971
    • Lepage, O.1    Kattnig, E.2    Fürstner, A.3
  • 22
    • 0030700685 scopus 로고    scopus 로고
    • For formation of trisubstituted (Z)-alkenes using Schrock's Mo catalyst, see: (g) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316 and references cited therein.
    • For formation of trisubstituted (Z)-alkenes using Schrock's Mo catalyst, see: (g) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316 and references cited therein.
  • 24
    • 0346850024 scopus 로고    scopus 로고
    • For use of RCM in total synthesis of amphidinolides E, T1, T3, T4, and T5, see: (i) Aïssa, C.; Riveiros, R.; Ragot, J.; Fürstner, A. J. Am. Chem. Soc. 2003, 125, 15512-15520 and references cited therein.
    • For use of RCM in total synthesis of amphidinolides E, T1, T3, T4, and T5, see: (i) Aïssa, C.; Riveiros, R.; Ragot, J.; Fürstner, A. J. Am. Chem. Soc. 2003, 125, 15512-15520 and references cited therein.
  • 25
    • 33846594323 scopus 로고    scopus 로고
    • arid references cited therein
    • (j) Va, P.; Roush, W. R. Org. Lett. 2007, 9, 307-310 arid references cited therein.
    • (2007) Org. Lett , vol.9 , pp. 307-310
    • Va, P.1    Roush, W.R.2
  • 29
    • 0000746743 scopus 로고
    • For anti-selective aldehyde crotylation. see: a
    • For anti-selective aldehyde crotylation. see: (a) Brown, H. C.; Bhat, K. J. Am. Chem. Soc. 1986, 108, 293-294.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 293-294
    • Brown, H.C.1    Bhat, K.2
  • 42
    • 34547181267 scopus 로고    scopus 로고
    • 2 and 16 mol % dppf as the catalyst system (rt, 12 h) in 71% overall yield for the conversion of 10 to 4.
    • 2 and 16 mol % dppf as the catalyst system (rt, 12 h) in 71% overall yield for the conversion of 10 to 4.
  • 44
    • 0037178482 scopus 로고    scopus 로고
    • For application in total synthesis, see
    • (b) Inoue, T.; Liu, J.-F.; Buske, D.; Abiko, A. J. Org. Chem. 2002, 67, 5250-5256. For application in total synthesis, see:
    • (2002) J. Org. Chem , vol.67 , pp. 5250-5256
    • Inoue, T.1    Liu, J.-F.2    Buske, D.3    Abiko, A.4
  • 48
    • 34547198794 scopus 로고    scopus 로고
    • 4 as reported in ref 19 caused cleavage and migration of TES ether, which could be avoided by using Dibal-H.
    • 4 as reported in ref 19 caused cleavage and migration of TES ether, which could be avoided by using Dibal-H.
  • 58
    • 34547165914 scopus 로고    scopus 로고
    • Additional RCM reactions were investigated as given in Supporting Information
    • Additional RCM reactions were investigated as given in Supporting Information.
  • 59
    • 34547174647 scopus 로고    scopus 로고
    • The results of amphidinolide Y total synthesis were presented at 3rd Yoshimasa Hirata Memorial Lecture, Nagoya, Japan, Feb. 6, 2007.
    • The results of amphidinolide Y total synthesis were presented at 3rd Yoshimasa Hirata Memorial Lecture, Nagoya, Japan, Feb. 6, 2007.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.