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Volumn 74, Issue 19, 2009, Pages 7411-7416

The synthesis of velloziolide via Nicholas reaction based γ-carbonyl cations

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; CHEMICAL EQUATIONS; CUPRATES; DITERPENES; JOHNSON-CLAISEN REARRANGEMENTS; MODEL STUDY; NICHOLAS REACTIONS; TOTAL SYNTHESIS;

EID: 70349451715     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901471b     Document Type: Article
Times cited : (18)

References (45)
  • 12
    • 0026065220 scopus 로고
    • For γ-carbonyl cation equivalents by way of iron allyl and dienyl cations, see: (a)
    • For γ-carbonyl cation equivalents by way of iron allyl and dienyl cations, see: (a) Green, J. R.; Carroll, M. K. Tetrahedron Lett. 1991, 32, 1141-1144.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1141-1144
    • Green, J.R.1    Carroll, M.K.2
  • 16
    • 0013319694 scopus 로고
    • and references therein
    • (e) Pearson, A. J. Adv. Met.-Org. Chem. 1988, 1, 1-49, and references therein.
    • (1988) Adv. Met.-Org. Chem. , vol.1 , pp. 1-49
    • Pearson, A.J.1
  • 18
    • 27644507981 scopus 로고    scopus 로고
    • For γ-carbonyl cation equivalents by way of π-allylpalladium complexes, see: (a)
    • For γ-carbonyl cation equivalents by way of π-allylpalladium complexes, see: (a) Nemoto, T.; Fukuda, T.; Matsumoto, T.; Hitomi, T.; Hamada, Y. Adv. Synth. Catal. 2005, 347, 1504-1506.
    • (2005) Adv. Synth. Catal. , vol.347 , pp. 1504-1506
    • Nemoto, T.1    Fukuda, T.2    Matsumoto, T.3    Hitomi, T.4    Hamada, Y.5
  • 20
    • 51549121546 scopus 로고    scopus 로고
    • For γ-carbonyl cation equivalents by way of carbonyl-substituted cyclopropanes, see: (a) and references therein
    • For γ-carbonyl cation equivalents by way of carbonyl-substituted cyclopropanes, see: (a) Lifchits, O.; Alberico, D.; Zakharian, I.; Charette, A. B. J. Org. Chem. 2008, 73, 6838-6840 and references therein.
    • (2008) J. Org. Chem. , vol.73 , pp. 6838-6840
    • Lifchits, O.1    Alberico, D.2    Zakharian, I.3    Charette, A.B.4
  • 23
    • 33847393177 scopus 로고    scopus 로고
    • For recent reviews dedicated to the Nicholas reaction, see: (a)
    • For recent reviews dedicated to the Nicholas reaction, see: (a) Diaz, D. D.; Betancort, J. M.; Martin, V. S. Synlett 2007, 343-353.
    • (2007) Synlett , pp. 343-353
    • Diaz, D.D.1    Betancort, J.M.2    Martin, V.S.3
  • 25
    • 0034912138 scopus 로고    scopus 로고
    • For reviews covering Nicholas reactions in part
    • (c) Green, J. R. Curr. Org. Chem. 2001, 5, 809-826. For reviews covering Nicholas reactions in part,
    • (2001) Curr. Org. Chem. , vol.5 , pp. 809-826
    • Green, J.R.1
  • 34
    • 70349465569 scopus 로고    scopus 로고
    • note
    • TMS or TBS protecting groups gave lower yields of condensation products.
  • 41
    • 70349470486 scopus 로고    scopus 로고
    • Hiersemann, M., Nubbemeyer U., Eds.; Wiley-VCH: Weinheim, Germany; Chapter 6
    • (a) Langlois, Y. In The Claisen Rearrangement; Hiersemann, M., Nubbemeyer U., Eds.; Wiley-VCH: Weinheim, Germany; Chapter 6.
    • The Claisen Rearrangement
    • Langlois, Y.1
  • 42
  • 44
    • 70349447428 scopus 로고    scopus 로고
    • note
    • 2O as solvent also allowed the conjugate addition process to proceed (89% yield) but gave an isomeric mixture of 15 (Z:E=14:86).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.