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Volumn 70, Issue 22, 2005, Pages 8841-8853

Studies toward the total synthesis of vinigrol. Synthesis of the octalin ring

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; OLEFINS; REACTION KINETICS; SELF ASSEMBLY; SYNTHESIS (CHEMICAL);

EID: 27444433536     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051318i     Document Type: Article
Times cited : (42)

References (66)
  • 21
    • 0000447319 scopus 로고    scopus 로고
    • (b) For the first example of Diels-Alder reaction by self-assembly of the components on a Lewis acid, see: Ward, D. E.; Abaee, M. S. Org. Lett. 2000, 2, 3937.
    • (2000) Org. Lett. , vol.2 , pp. 3937
    • Ward, D.E.1    Abaee, M.S.2
  • 23
    • 0032510338 scopus 로고    scopus 로고
    • and references therein
    • (a) For a review on tethers in cycloadditions, see: Shea, K. J.; Zandi, K. S.; Gauthier, D. R. Tetrahedron 1998, 54, 2289 and references therein.
    • (1998) Tetrahedron , vol.54 , pp. 2289
    • Shea, K.J.1    Zandi, K.S.2    Gauthier, D.R.3
  • 34
    • 27444439497 scopus 로고    scopus 로고
    • note
    • 1H NMR 300 and 500 MHz of the crude reaction mixture.
  • 39
    • 33845471185 scopus 로고
    • and references therein
    • Lutz, R. P. Chem. Rev. 1984, 84, 205 and references therein.
    • (1984) Chem. Rev. , vol.84 , pp. 205
    • Lutz, R.P.1
  • 44
    • 27444432814 scopus 로고    scopus 로고
    • note
    • During the course of this research, Paquette and co-workers also explored the formation of the cyclcooctane ring of vinigrol via RCM; see ref 3c
  • 49
    • 27444435281 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 38 was established by X-ray diffraction, For an ORTEP view of 38 (benzoate derivative), see the Supporting Information.
  • 59
    • 27444446752 scopus 로고    scopus 로고
    • note
    • The structure of 61f was established by NMR spectroscopy and confirmed by X-ray analysis. For ORTEP view of 61f, see the Supporting Information.
  • 60
    • 11144325118 scopus 로고    scopus 로고
    • For a review on microwaves in organic synthesis, see: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6250
    • Kappe, C.O.1
  • 65
    • 27444435100 scopus 로고    scopus 로고
    • note
    • Nonpolar solvents such as toluene do not absorb microwaves, and therefore, a glass-coated Carboflon was placed inside the reaction cell. Carboflon readily absorbs microwave energy and transmits heat to the reaction mixture through conduction. This microwave oven is equipped with a fiber optic probe placed inside the reaction cell to monitor the temperature and pressure of the reaction.
  • 66
    • 27444442206 scopus 로고    scopus 로고
    • note
    • For ORTEP view of 62, see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.