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Volumn 10, Issue 5, 2008, Pages 811-814

Total synthesis of aigialomycin D: Surprising chemoselectivity dependence on alkyne structure in nickel-catalyzed cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

AIGIALOMYCIN D; ALKENE; ALKYNE; MACROLIDE; NICKEL;

EID: 43549107787     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702961v     Document Type: Article
Times cited : (48)

References (38)
  • 14
    • 16244420717 scopus 로고    scopus 로고
    • For other studies ol'ynal macrocyclizations, see: a
    • For other studies ol'ynal macrocyclizations, see: (a) Colby, E. A.; O'Brien, K. C; Jamison, T. F. J. Am.'Chem. Soc. 2005, 127, 4297.
    • (2005) Am.'Chem. Soc , vol.127 , pp. 4297
    • Colby, E.A.1    O'Brien, K.C.2    Jamison, T.F.J.3
  • 19
    • 22244490357 scopus 로고    scopus 로고
    • For diastere©selective internal alkyne--aldehyde couplings: a
    • For diastere©selective internal alkyne--aldehyde couplings: (a) Luanphaisarnnont. T.; Ndubaku, C. O.; Jamison, T. F. Org. Lett. 2005, 7, 2937.
    • (2005) Org. Lett , vol.7 , pp. 2937
    • Luanphaisarnnont, T.1    Ndubaku, C.O.2    Jamison, T.F.3
  • 21
    • 33646464670 scopus 로고    scopus 로고
    • For applications in macrolicie synthesis
    • (c) For applications in macrolicie synthesis: Bahadoor. A. B.; Micalizio, G. C. Org. Lett. 2006, 8, 1181.
    • (2006) Org. Lett , vol.8 , pp. 1181
    • Bahadoor, A.B.1    Micalizio, G.C.2
  • 29
    • 4644370089 scopus 로고    scopus 로고
    • For observation of melallacycle generation from an aldehyde, alkene. and silyl triflate
    • For observation of melallacycle generation from an aldehyde, alkene. and silyl triflate: Ogoshi, S.; Oka, M.-A.; Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 11802
    • Ogoshi, S.1    Oka, M.-A.2    Kurosawa, H.3
  • 30
    • 26844515782 scopus 로고    scopus 로고
    • For development of the catalytic coupling of aldehydes, alkenes, and silvl triflates: a
    • For development of the catalytic coupling of aldehydes, alkenes, and silvl triflates: (a) Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 14194.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 14194
    • Ng, S.-S.1    Jamison, T.F.2
  • 34
    • 58149190430 scopus 로고    scopus 로고
    • A tentative possibility is that triethylsilane undergoes nickel-catalyzed conversion to triethylsilanol in the presence of water to generate the Et 3SiX species depicted in Scheme 3. Control experiments illustrated that Et3SiOH is slowly produced under the reaction conditions in the absence of substrate 2
    • 3SiOH is slowly produced under the reaction conditions in the absence of substrate 2.
  • 35
    • 58149198781 scopus 로고    scopus 로고
    • For a detailed study of the role of the acceleration of oxidative cyclizations by Lewis acids see: Hratchian. H. P.; Chowdhury. S. K.; Gutiérre;z-García, V. M.; Amarasinghe. K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636.
    • (a) For a detailed study of the role of the acceleration of oxidative cyclizations by Lewis acids see: Hratchian. H. P.; Chowdhury. S. K.; Gutiérre;z-García, V. M.; Amarasinghe. K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636.
  • 37
    • 58149198782 scopus 로고    scopus 로고
    • Simple intermolecuiar reductive couplings of benzaldehyde with either styrene or allyl benzene are not promoted by either Et3SiH in wet THF or Et3SiOH in dry THF with use of the catalyst and reaction conditions used in the production of 10
    • 3SiOH in dry THF with use of the catalyst and reaction conditions used in the production of 10.
  • 38
    • 58149198180 scopus 로고    scopus 로고
    • Additional synthetic manipulations of compounds derived from 19 were performed for the confirmation of structure 20. See the Supporting Information for details.
    • Additional synthetic manipulations of compounds derived from 19 were performed for the confirmation of structure 20. See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.