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Volumn 12, Issue 12, 2010, Pages 2746-2749

Seebach's conjunctive reagent enables double cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

CITRINADIN A; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; INDOLE ALKALOID; KETONE;

EID: 77953570312     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100845z     Document Type: Article
Times cited : (14)

References (49)
  • 2
    • 77953563001 scopus 로고    scopus 로고
    • For ring annulations via the reactions of dimethyl γ- bromomesaconate with enamines of cyclic ketones, see
    • For ring annulations via the reactions of dimethyl γ- bromomesaconate with enamines of cyclic ketones, see
  • 4
    • 77953589340 scopus 로고    scopus 로고
    • For a one-pot synthesis of adamantane derivatives via a bimolecular coupling with four bond formations, see
    • For a one-pot synthesis of adamantane derivatives via a bimolecular coupling with four bond formations, see
  • 6
    • 77953592058 scopus 로고    scopus 로고
    • For a ring annulation with three bond formations in a synthesis of clusianone, see
    • For a ring annulation with three bond formations in a synthesis of clusianone, see
  • 8
    • 77953593258 scopus 로고    scopus 로고
    • For the use of 2-bromoethyl-3-(trimethylsilylmethyl)buta-1,3-diene in tandem annulations, see
    • For the use of 2-bromoethyl-3-(trimethylsilylmethyl)buta-1,3-diene in tandem annulations, see
  • 10
    • 77953607998 scopus 로고    scopus 로고
    • For uses of 2-nitro-3-pivaloyloxypropene to achieve ring annulations, see
    • For uses of 2-nitro-3-pivaloyloxypropene to achieve ring annulations, see
  • 15
    • 77953576137 scopus 로고    scopus 로고
    • The Martin laboratory achieved a concise and stereocontrolled synthesis of the spirooxindole ring system of citrinadin A; see
    • The Martin laboratory achieved a concise and stereocontrolled synthesis of the spirooxindole ring system of citrinadin A; see
  • 23
    • 77953560980 scopus 로고    scopus 로고
    • For selected examples of conjunctive reagents (also known as "linchpin" or "multiple coupling" reagents), see
    • For selected examples of conjunctive reagents (also known as "linchpin" or "multiple coupling" reagents), see
  • 30
    • 0001564507 scopus 로고
    • For a review of tandem vicinal difunctionalizations, see
    • For a review of tandem vicinal difunctionalizations, see: Chapdelaine, M. J.; Hulce, M. Org. React. (N.Y.) 1990, 38, 225
    • (1990) Org. React. (N.Y.) , vol.38 , pp. 225
    • Chapdelaine, M.J.1    Hulce, M.2
  • 44
    • 77953562342 scopus 로고    scopus 로고
    • Additional bases could also effect unions of compound 9 with NPP reagent 4. See the Supporting Information for details
    • Additional bases could also effect unions of compound 9 with NPP reagent 4. See the Supporting Information for details.
  • 46
    • 77953589339 scopus 로고    scopus 로고
    • note
    • The use of a stronger base (NaHMDS) in the generation of compounds 20 and 28 was required to afford the desired double cyclization. In the absence of this added base, compounds of type 6 shown in Scheme 2 are isolated.
  • 48
    • 77953587021 scopus 로고    scopus 로고
    • note
    • Support for a bonding interaction between proximate hydroxyl and nitro groups may be found in the significantly lower boiling point of o -nitrophenol (216 °C) in relation to p -nitrophenol (279 °C).


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