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Volumn 11, Issue 2, 2009, Pages 353-356

Toward the total synthesis of the brasilinolides: Stereocontrolled assembly of a C1-C19 polyol segment

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; CARBON; MACROLIDE; POLYMER; POLYOL;

EID: 61449179275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802562b     Document Type: Article
Times cited : (23)

References (27)
  • 5
    • 0034891425 scopus 로고    scopus 로고
    • For a review of the chemistry and biology of immunosuppressive natural products, see
    • For a review of the chemistry and biology of immunosuppressive natural products, see: Mann, J. Nat. Prod. Rep. 2001, 18, 417.
    • (2001) Nat. Prod. Rep , vol.18 , pp. 417
    • Mann, J.1
  • 8
    • 0000271703 scopus 로고    scopus 로고
    • For related studies from the Evans group, see: a
    • For related studies from the Evans group, see: (a) Evans, D. A.; Coleman, P. J.; Côté, B. J. Org. Chem. 1997, 62, 788.
    • (1997) J. Org. Chem , vol.62 , pp. 788
    • Evans, D.A.1    Coleman, P.J.2    Côté, B.3
  • 16
    • 62149125944 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 23
    • 0001951357 scopus 로고    scopus 로고
    • 13C NMR analysis using Rychnovsky's method and (ii) treatment of 17 with DDQ to generate the corresponding 5,7-syn PMP acetal and NOE analysis. Rychnovsky, S.D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
    • 13C NMR analysis using Rychnovsky's method and (ii) treatment of 17 with DDQ to generate the corresponding 5,7-syn PMP acetal and NOE analysis. Rychnovsky, S.D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
  • 24
    • 39349099300 scopus 로고    scopus 로고
    • We thank Dr. Rob Paton for carrying out transition state calculations for R1, Me and R2, E-CH=CHMe, where TS-I leading to adduct 21 was preferred. Paton, R. S, Goodman, J. M. J. Org. Chem. 2008, 73, 1253
    • 2 = (E)-CH=CHMe, where TS-I leading to adduct 21 was preferred. Paton, R. S.; Goodman, J. M. J. Org. Chem. 2008, 73, 1253.
  • 25
    • 2142858450 scopus 로고    scopus 로고
    • The configuration was determined by use of the advanced Mosher method: Ohtani, I.; Kasumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
    • The configuration was determined by use of the advanced Mosher method: Ohtani, I.; Kasumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
  • 26
    • 84987464056 scopus 로고    scopus 로고
    • The use of an indicator (Sudan red 7B) was crucial to prevent oxidation of the PMB ethers. Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807.
    • The use of an indicator (Sudan red 7B) was crucial to prevent oxidation of the PMB ethers. Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807.
  • 27
    • 62149139428 scopus 로고    scopus 로고
    • The spectroscopic data of 2 matched that of material prepared via the route described in Scheme 4.
    • The spectroscopic data of 2 matched that of material prepared via the route described in Scheme 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.