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Volumn 9, Issue 13, 2007, Pages 2597-2600

The total synthesis of psymberin

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PSYMBERIN; PYRAN DERIVATIVE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34547153679     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071068n     Document Type: Article
Times cited : (59)

References (24)
  • 3
    • 23844506416 scopus 로고    scopus 로고
    • Total synthesis, see: a, 11254 and references cited therein. Formal total synthesis, see
    • Total synthesis, see: (a) Jiang, X.; Garcia-Fortanet, J.; De Brabander, J. K. J. Am. Chem. Soc. 2005, 127, 11254 and references cited therein. Formal total synthesis, see:
    • (2005) J. Am. Chem. Soc , vol.127
    • Jiang, X.1    Garcia-Fortanet, J.2    De Brabander, J.K.3
  • 7
    • 22244436600 scopus 로고    scopus 로고
    • 2905. Analogue synthesis, see
    • (e) Kiren, S.; Williams, L. J. Org. Lett. 2005, 7, 2905. Analogue synthesis, see:
    • (2005) Org. Lett , vol.7
    • Kiren, S.1    Williams, L.J.2
  • 10
    • 0033575406 scopus 로고    scopus 로고
    • 6 was prepared from commercially available 2,4,6-trimethoxytoluene in two steps in 46% yield according to literature procedure. Solladie, G.: Gehrold, N.; Maignan, J. Tetrahedron: Asymmetry 1999, 10, 2739.
    • 6 was prepared from commercially available 2,4,6-trimethoxytoluene in two steps in 46% yield according to literature procedure. Solladie, G.: Gehrold, N.; Maignan, J. Tetrahedron: Asymmetry 1999, 10, 2739.
  • 14
    • 34547182301 scopus 로고    scopus 로고
    • Although we did not proceed with compound 3 for the total synthesis, it was prepared efficiently from 14 in 7 steps (Scheme 4) and served as a vehicle to determine the correct sterochemistry at C5 by spectrum comparison with the psymberin side chain.2d,e
    • 2d,e
  • 15
    • 34547195715 scopus 로고    scopus 로고
    • All compounds containing this side chain were a 1:1 mixture of two isomers (R, S) at C: except when otherwise indicated.
    • All compounds containing this side chain were a 1:1 mixture of two isomers (R, S) at C: except when otherwise indicated.
  • 19
    • 34547178752 scopus 로고    scopus 로고
    • 15 acetonide from the corresponding hydroxy derivatives of 18.
    • 15 acetonide from the corresponding hydroxy derivatives of 18.
  • 21
    • 34547189098 scopus 로고    scopus 로고
    • It is not necessary to separate the E and Z isomers since they work equally well in the oxidative cyclization reaction. See ref 3
    • It is not necessary to separate the E and Z isomers since they work equally well in the oxidative cyclization reaction. See ref 3.
  • 23
    • 34547177710 scopus 로고    scopus 로고
    • The R,R stereochemistry at Cx, CY was assigned by using COSY, NOESY, HSQC, and HMBC experiments with the final product epi-1, see the Supporting Information.
    • The R,R stereochemistry at Cx, CY was assigned by using COSY, NOESY, HSQC, and HMBC experiments with the final product epi-1, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.