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Volumn 125, Issue 50, 2003, Pages 15443-15454

Total Synthesis of Apoptolidin: Completion of the Synthesis and Analogue Synthesis and Evaluation

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; SYNTHESIS (CHEMICAL); TUMORS;

EID: 10744222793     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030496v     Document Type: Article
Times cited : (98)

References (41)
  • 6
    • 0142236572 scopus 로고    scopus 로고
    • Low Mode Search
    • The authors thank Dr. Chenglong Li for these calculations. For details of the calculation method employed, see: Kolossváry, I.; Guida, W. C. Low Mode Search. J. Am. Chem. Soc. 1996, 118, 5011-5019.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5011-5019
    • Kolossváry, I.1    Guida, W.C.2
  • 11
    • 0003083944 scopus 로고
    • For reviews of the Horner-Wadsworth-Emmons reaction, see: (a) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-254.
    • (1977) Org. React. , vol.25 , pp. 73-254
    • Wadsworth Jr., W.S.1
  • 16
    • 0027465280 scopus 로고
    • For representative examples of asymmetric dihydroxylation of electron-deficient olefins, see: (a) Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 2079-2082.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2079-2082
    • Bennani, Y.L.1    Sharpless, K.B.2
  • 21
    • 0346657272 scopus 로고    scopus 로고
    • note
    • 1H NMR, IR and MS spectrometry.
  • 22
    • 0000383342 scopus 로고    scopus 로고
    • 9 hydroxy group was protected (as TBS or TMS ethers or acetate) were not successful. For related observations and alternative coupling conditions, see also: Schuppan, J.; Wehlan, H.; Keiper, S.; Koert, U. Angew. Chem., Int. Ed. 2001, 40, 2063-2066.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2063-2066
    • Schuppan, J.1    Wehlan, H.2    Keiper, S.3    Koert, U.4
  • 25
    • 0031799661 scopus 로고    scopus 로고
    • For Stille coupling reactions on related vinylstannanes with free allylic hydroxy groups, see: (c) Betzer, J.-F.; Lallemand, J.-Y.; Pancrazi, A. Synthesis 1998, 522-534.
    • (1998) Synthesis , pp. 522-534
    • Betzer, J.-F.1    Lallemand, J.-Y.2    Pancrazi, A.3
  • 34
    • 0346026165 scopus 로고    scopus 로고
    • note
    • Samples of apoptolidin were kindly provided by Professor C. Khosla of Stanford University.
  • 35
    • 0037669297 scopus 로고    scopus 로고
    • Wender and co-workers reported an alternative way to prepare apoptolidin methyl glycoside from the natural product, see: Wender, P. A.; Jankowski, O. D. ; Tabet, E. A.; Seto, H. Org. Lett. 2003, 5, 487-490.
    • (2003) Org. Lett. , vol.5 , pp. 487-490
    • Wender, P.A.1    Jankowski, O.D.2    Tabet, E.A.3    Seto, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.