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Volumn 70, Issue 12, 2005, Pages 4762-4773

Total synthesis of the potent antitumor polyketide (-)-callystatin A

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; KETONES; TUMORS;

EID: 20344378226     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050352u     Document Type: Article
Times cited : (57)

References (71)
  • 16
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    • For a very interesting review on the chemistry and biology of the leptomycin family, see: Kaiesse, M.; Christmann, M. Synthesis 2002, 981.
    • (2002) Synthesis , pp. 981
    • Kaiesse, M.1    Christmann, M.2
  • 20
    • 0033546380 scopus 로고    scopus 로고
    • For a previous synthesis of the C13-C22 fragment of callystatin A, see: (a) Marshall, J. A.; Fitzgerald, R. N. J. Org. Chem. 1999, 64, 4477.
    • (1999) J. Org. Chem. , vol.64 , pp. 4477
    • Marshall, J.A.1    Fitzgerald, R.N.2
  • 23
    • 20344384153 scopus 로고    scopus 로고
    • note
    • Numbering of 1 as well as of each intermediate follows that suggested in ref 1.
  • 39
    • 0037000811 scopus 로고    scopus 로고
    • For a recent review with several examples of α-pyrones prepared using ring-closing metathesis (RCM), see: Ramachandran, P. V. Aldrichim. Acta 2002, 35, 23.
    • (2002) Aldrichim. Acta , vol.35 , pp. 23
    • Ramachandran, P.V.1
  • 40
    • 0025128154 scopus 로고
    • Aldehyde 18 was prepared in three steps and 77% overall yield from (R)-methyl-3-hydroxy-propanoate following protection with TBDPSC1 and imidazole, reduction of the ester to the primary alcohol with excess DIBAL-H, followed by Swern oxidation. See Supporting Information for details. (a) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 0348.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 0348
    • Roush, W.R.1    Palkowitz, A.D.2    Ando, K.3
  • 42
    • 0035909645 scopus 로고    scopus 로고
    • For an interesting paper dealing with the construction of the C8-C9 (Z)-trisubstituted olefm of callystatin A and analogues, see: Arefolov, A.; Languie, N. F.; Panek, J. S. Org. Lett. 2001, 3, 3281.
    • (2001) Org. Lett. , vol.3 , pp. 3281
    • Arefolov, A.1    Languie, N.F.2    Panek, J.S.3
  • 62
    • 20344374886 scopus 로고    scopus 로고
    • note
    • Relative stereochemistry for 32 was further confirmed after transformation to vinyl iodide 39, previously described by Marshall and Bourbeau in their elegant synthesis of (-)-callystatin A. See ref 4f.
  • 71
    • 20344390903 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR, HRMS, and analytical data. Yields refer to chromatographically and spectroscopically homogeneous materials.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.