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Volumn 125, Issue 42, 2003, Pages 12836-12843

A Second-Generation Synthesis of the C1-C28 Portion of the Altohyrtins (Spongistatins)

Author keywords

[No Author keywords available]

Indexed keywords

SECOND-GENERATION SYNTHESIS;

EID: 0142040638     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030316h     Document Type: Article
Times cited : (60)

References (84)
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    • For leading references to synthetic approaches from other laboratories, see the list in ref 16, plus the following: (a) Zuev, D.; Paquette, L. A. Org. Lett. 2000, 2, 679-682.
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    • Zuev, D.1    Paquette, L.A.2
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    • The enantiomer of 9 was used. see ref 15
    • The enantiomer of 9 was used. see ref 15.
  • 51
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    • note
    • 3.
  • 52
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    • note
    • Use of tributylphosphine as the reducing agent minimized methanolysis of the acetal in this step.
  • 53
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    • Tse, B. J. Am. Chem. Soc. 1996, 118, 7094. Compound 15 is also commercially available from the Aldrich Chemical Co.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7094
    • Tse, B.1
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    • 0142050791 scopus 로고    scopus 로고
    • note
    • 3, pyridine; IBX; PDC; TPAP, NMO; Dess-Martin, pyridine.
  • 57
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    • Problems with oxidation of aldol products under Dess-Martin conditions have been noted previously: Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
    • (1994) J. Org. Chem. , vol.59 , pp. 7549
    • Meyer, S.D.1    Schreiber, S.L.2
  • 58
    • 0000596196 scopus 로고    scopus 로고
    • The oxidation of diketones by iodine-III species is a well-known process, see for a review: Moriarty, R. M.; Prakash, O. Org. React. 1999, 54, 273. We have also isolated the triketone product in a similar system: Claffey, M. M.; Heathcock, C. H., unpublished results.
    • (1999) Org. React. , vol.54 , pp. 273
    • Moriarty, R.M.1    Prakash, O.2
  • 61
    • 0142018847 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for the reactions used and yields obtained in the preparation of 19 and 22.
  • 67
    • 0142114107 scopus 로고    scopus 로고
    • note
    • Care had to be taken to avoid overreduction to the alkane; TLC analysis with 30% ethyl acetate in benzene separates the alkene from the overreduced product.
  • 69
    • 0142050790 scopus 로고    scopus 로고
    • note
    • Recall that our first-generation spiroketalization substrate had one more carbon in the chain, making the TBS ether in that case significantly less sterically hindered.
  • 70
    • 0142114108 scopus 로고    scopus 로고
    • note
    • Migration of the pivaloyl protecting group to the secondary alcohol was observed during the epoxide opening when the more direct route from glycidol pivalate was attempted.
  • 73
    • 0142114109 scopus 로고    scopus 로고
    • note
    • 3 and MeI did not effect the desired reaction so NaH was added to the reaction mixture.
  • 74
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    • Stereoelectronic Effects in Organic Chemistry
    • Baldwin, J. E., Ed.; Pergamon Press: Oxford
    • Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry. In Organic Chemistry Series; Baldwin, J. E., Ed.; Pergamon Press: Oxford, 1989; Vol. 1.
    • (1989) Organic Chemistry Series , vol.1
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    • note
    • The same stereoelectronic preference operates in the formation of the A/ B spiroketal 18 (Scheme 4). In that case, axial addition of the C11 hydroxy group should give the observed S spiroketal because addition should be trans to the substituent at C3. which in this case has the R configuration.
  • 82
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    • For examples in which proximal heteroatom substituents stabilize glycosides with respect to acid-catalyzed hydrolysis, see: (a) Roush, W. R.; Lin, X.-F. J. Am. Chem. Soc. 1995, 117, 2236.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2236
    • Roush, W.R.1    Lin, X.-F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.