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Volumn 71, Issue 13, 2006, Pages 4929-4936

Rearrangement of 4,5-epoxy-9-trimethylsilyldecalines. Application to the synthesis of the natural eremophilane (-)-aristolochene

Author keywords

[No Author keywords available]

Indexed keywords

ARISTOLOCHENE; EREMOPHILANE; OXIRANE RING; TRIMETHYLSILYLDECALINES;

EID: 33745451697     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060643i     Document Type: Article
Times cited : (15)

References (45)
  • 1
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    • and previous reviews in this series
    • (a) Dewick, P. M. Nat. Prod. Rep. 2002, 19, 181-222 and previous reviews in this series,
    • (2002) Nat. Prod. Rep. , vol.19 , pp. 181-222
    • Dewick, P.M.1
  • 31
    • 0003417469 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • Rao, A. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1993; Vol. 7.
    • (1993) Comprehensive Organic Synthesis , vol.7
    • Rao, A.S.1
  • 35
    • 33745446917 scopus 로고    scopus 로고
    • note
    • Catalytic hydrogenation attempts with Pd/C or Wilkinson's catalyst resulted in the hydrogenolysis of the allyl C-O bond.
  • 37
    • 33745461627 scopus 로고    scopus 로고
    • note
    • The stereochemistry of epoxide 7b was assigned on the assumption of a preferential attack of the epoxidating reagent from the α side of the molecule, opposite to the isopropyl chain, as it was proved in compounds 7a and 20. See also a discussion on the stereochemistry of compound 20 in the text.
  • 40
    • 33745450936 scopus 로고    scopus 로고
    • note
    • The reasons for the slow elimination of the TMS group in (iii) are not clear at the moment, but it may be due to a lack of coplanarity between the involved orbitals of the C-Si bond and the carbocation. This would permit successive rearrangements from (iii) to (v) that would relieve the angular strain associated with the spiranic carbon and would lead to a final carbocation (v) stabilized by the TMS and also by the neighboring alkoxide.
  • 43
    • 0003737513 scopus 로고
    • Oxford University: Oxford
    • 6 slows down the exchange of the hydroxyl proton so it gives a defined signal that can be irradiated in NOE experiments: Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy; Oxford University: Oxford, 1989.
    • (1989) Modern NMR Spectroscopy
    • Sanders, J.K.M.1    Hunter, B.K.2
  • 45
    • 33745471402 scopus 로고    scopus 로고
    • note
    • For a description of the general experimental methods, see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.