메뉴 건너뛰기




Volumn 72, Issue 8, 2007, Pages 2945-2950

Bicyclic β-hydroxytetrahydrofurans as precursors of medium ring keto-lactones

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLDIOXIRANE; MEDIUM RING KETO-LACTONES; SODIUM PERIODATE;

EID: 34247262138     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0626109     Document Type: Article
Times cited : (27)

References (49)
  • 10
    • 0034246704 scopus 로고    scopus 로고
    • Yet, L. Chem. Rev. 2000, 100, 2963.
    • (2000) Chem. Rev , vol.100 , pp. 2963
    • Yet, L.1
  • 19
    • 33645364955 scopus 로고    scopus 로고
    • The general methodology for macrolactones synthesis can often be applied for medium ring lactones. For a recent review: Parenty, A.; Moreau, X.; Campagne, J. M. Chem. Rev. 2006, 106, 911.
    • The general methodology for macrolactones synthesis can often be applied for medium ring lactones. For a recent review: Parenty, A.; Moreau, X.; Campagne, J. M. Chem. Rev. 2006, 106, 911.
  • 21
    • 26844563263 scopus 로고    scopus 로고
    • For a review concerning ruthenium tetraoxide-catalyzed oxidations
    • For a review concerning ruthenium tetraoxide-catalyzed oxidations: Plietker, B. Synthesis 2005, 2453.
    • (2005) Synthesis , pp. 2453
    • Plietker, B.1
  • 22
    • 33644645804 scopus 로고
    • and references cited therein
    • Drees, M.; Strassner, T. J. Org. Chem. 2006, 71, 1755 and references cited therein.
    • (1755) J. Org. Chem , vol.71
    • Drees, M.1    Strassner, T.2
  • 25
    • 9344260283 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Plietker, B. J. Org. Chem. 2004, 69, 8287 and references cited therein.
    • (2004) J. Org. Chem , vol.69 , pp. 8287
    • Plietker, B.1
  • 30
    • 0141740698 scopus 로고    scopus 로고
    • Part of this work was reported as a preliminary communication: Ferraz, H. M. C.; Longo, L. S., Jr. Org. Lett. 2003, 5, 1337.
    • Part of this work was reported as a preliminary communication: Ferraz, H. M. C.; Longo, L. S., Jr. Org. Lett. 2003, 5, 1337.
  • 33
    • 34247181354 scopus 로고    scopus 로고
    • For experimental details and full characterization data of 1a, 1b, and 1d see ref 27. For a general procedure for the preparation of 1c, 1e, and 1f, see Supporting Information
    • For experimental details and full characterization data of 1a, 1b, and 1d see ref 27. For a general procedure for the preparation of 1c, 1e, and 1f, see Supporting Information.
  • 35
    • 34247229868 scopus 로고    scopus 로고
    • Performing the reaction with 4.0 equiv of NaH in anhydrous THF led to the exclusive formation of the allylic alcohol 5 along with recovered starting material after 3 h under reflux. It is noteworthy that 5 was the only regioisomer observed with either KOH or NaH.
    • Performing the reaction with 4.0 equiv of NaH in anhydrous THF led to the exclusive formation of the allylic alcohol 5 along with recovered starting material after 3 h under reflux. It is noteworthy that 5 was the only regioisomer observed with either KOH or NaH.
  • 36
    • 2542433188 scopus 로고    scopus 로고
    • The use of acetonitrile, as established by Sharpless and co-workers, represents a great improvement in the reaction protocol, since this solvent can prevent coordination of low-valent ruthenium species with carboxylic acids formed as byproducts during the course of the reaction. Carlsen, H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
    • The use of acetonitrile, as established by Sharpless and co-workers, represents a great improvement in the reaction protocol, since this solvent can prevent coordination of low-valent ruthenium species with carboxylic acids formed as byproducts during the course of the reaction. Carlsen, H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
  • 37
    • 34247235840 scopus 로고    scopus 로고
    • A saturated aqueous solution of sodium sulfite (Na2SO 3) is also used in the workup protocols of ruthenium tetraoxide-mediated oxidations see ref 22
    • 3) is also used in the workup protocols of ruthenium tetraoxide-mediated oxidations (see ref 22).
  • 38
    • 34247188745 scopus 로고    scopus 로고
    • For the 1H and 13C NMR spectra of the keto-lactones 7g-j see ref 26
    • 13C NMR spectra of the keto-lactones 7g-j see ref 26.
  • 44
    • 0026572386 scopus 로고    scopus 로고
    • Diketone 10 exists predominantly in the enol form: Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1992, 114, 1790.
    • Diketone 10 exists predominantly in the enol form: Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1992, 114, 1790.
  • 45
    • 34247254009 scopus 로고    scopus 로고
    • For experimental details and full characterization data of products 11 and 12 see Supporting Information.
    • For experimental details and full characterization data of products 11 and 12 see Supporting Information.
  • 47
    • 34247239505 scopus 로고    scopus 로고
    • An example of the RuO4-promoted oxidation of a formate ester to the corresponding ketone is described in ref 25
    • 4-promoted oxidation of a formate ester to the corresponding ketone is described in ref 25.
  • 48
    • 34247280160 scopus 로고    scopus 로고
    • 2O were based on n = 1.
    • 2O were based on n = 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.