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Volumn 62, Issue 22, 2006, Pages 5215-5222

Synthesis of five- to seven-membered polyfunctional terpenic carbocycles via Ti(III)-catalyzed radical cyclizations of epoxypolyprenes

Author keywords

Cyclization; Epoxides; Radical reaction; Terpenoids; Titanium

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; PYRENE DERIVATIVE; TERPENE DERIVATIVE;

EID: 33646137398     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.067     Document Type: Article
Times cited : (23)

References (42)
  • 24
    • 33646121656 scopus 로고    scopus 로고
    • note
    • Nerolidol was obtained from the essential oil of Baccharis tricuneata var. ruiziana, collected in Cochabamba, Bolivia.
  • 27
    • 33646162326 scopus 로고
    • Connolly J.D., and Hill R.A. (Eds), Chapman and Hall, London, UK
    • In: Connolly J.D., and Hill R.A. (Eds). Dictionary of Terpenoids, Vol. 2 (1991), Chapman and Hall, London, UK 1282
    • (1991) Dictionary of Terpenoids, Vol. 2 , pp. 1282
  • 28
    • 33646138148 scopus 로고    scopus 로고
    • note
    • 2Ti(Cl)H and oxygen-bonded titanium derivatives.
  • 29
    • 33646140034 scopus 로고    scopus 로고
    • For previous 6-endo/5-exo sequences, see:
  • 32
    • 33646135217 scopus 로고    scopus 로고
    • note
    • 2D-NMR, including NOESY experiments allowed us to establish the relative configurations in 13 and 14.
  • 33
    • 33646153907 scopus 로고    scopus 로고
    • note
    • For compounds 13 and 14, the difference in energy between their most stable conformations and the closer ones in energy is around 6 kcal/mol.
  • 35
    • 0001154351 scopus 로고
    • Previous experiments carried out in our laboratory with 6,7-epoxylinalyl acetate afforded good yield of the corresponding seven-membered carbocycle. A Thorpe-Ingold effect exerted by the methyl and acetate group upon C-3 carbon was postulated to rationalize this result, see Ref. 3. For other 7-endo radical cyclizations, see:
    • Previous experiments carried out in our laboratory with 6,7-epoxylinalyl acetate afforded good yield of the corresponding seven-membered carbocycle. A Thorpe-Ingold effect exerted by the methyl and acetate group upon C-3 carbon was postulated to rationalize this result, see Ref. 3. For other 7-endo radical cyclizations, see:. Crich D., and Fortt S.M. Tetrahedron 45 (1989) 6581-6589
    • (1989) Tetrahedron , vol.45 , pp. 6581-6589
    • Crich, D.1    Fortt, S.M.2
  • 36
    • 33646142213 scopus 로고    scopus 로고
    • For cationic examples of 7-endo cyclizations, see for the following syntheses of serratenediol:
  • 40
    • 33646143685 scopus 로고    scopus 로고
    • note
    • 2O, starting material, and 23 were obtained with high yields in an equimolecular ratio.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.