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Volumn 5, Issue 26, 2003, Pages 5035-5038

Leucascandrolide A: A Second Generation Formal Synthesis

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; LEUCASCANDROLIDE A; UNCLASSIFIED DRUG;

EID: 0346025396     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036071v     Document Type: Article
Times cited : (47)

References (44)
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    • (c) Paterson, I.; Tudge, M. Angew. Chem., Int. Ed. 2003, 42, 343. Paterson, I.; Tudge, M. Tetrahedron 2003, 59, 6833.
    • (2003) Tetrahedron , vol.59 , pp. 6833
    • Paterson, I.1    Tudge, M.2
  • 8
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    • ASAP Article
    • (d) Fettes, A.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 4098. Fettes, A.; Carreira, E. M. J. Org. Chem. 2003, ASAP Article.
    • (2003) J. Org. Chem.
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    • For additional examples: (a) Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251. (b) Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chern. Soc. 1999, 121, 4924. (c) Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7251
    • Williams, D.R.1    Brooks, D.A.2    Meyer, K.G.3    Clark, M.P.4
  • 14
    • 0033606291 scopus 로고    scopus 로고
    • For additional examples: (a) Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251. (b) Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chern. Soc. 1999, 121, 4924. (c) Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765.
    • (1999) J. Am. Chern. Soc. , vol.121 , pp. 4924
    • Williams, D.R.1    Brooks, D.A.2    Berliner, M.A.3
  • 15
    • 0035977646 scopus 로고    scopus 로고
    • For additional examples: (a) Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251. (b) Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chern. Soc. 1999, 121, 4924. (c) Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 765
    • Williams, D.R.1    Meyer, K.G.2
  • 19
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    • see ref 5a
    • The stereochemistry of 7 was assigned by protodesilyation and comparison with known material (see ref 5a).
  • 21
    • 0038476066 scopus 로고    scopus 로고
    • Scheffold, R.; Saladin, E. Angew. Chem., Int. Ed. Engl. 1972, 11, 229. For a recent application, see: Harmata, M.; Bohnert, G. J. Org. Lett. 2003, 5, 59.
    • (2003) Org. Lett. , vol.5 , pp. 59
    • Harmata, M.1    Bohnert, G.J.2
  • 26
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    • note
    • Our molecular modelling indicates nonbonded interactions of the axially disposed aldehydic H and the sulfonyl oxygens in 16.
  • 27
    • 0347908763 scopus 로고    scopus 로고
    • In press
    • Stereogenecity in the starting stannane, which positions a chiral center at the β-carbon of the C-2 appendage with respect to the allyl nucleophile (or is more remote), does not affect the diastereofacial selectivity imposed by the auxiliary. For a full account of this work, see: Williams, D. R.; Meyer, K. G.; Shamim, K.; Patnaik, S. Can. J. Chem. In press.
    • Can. J. Chem.
    • Williams, D.R.1    Meyer, K.G.2    Shamim, K.3    Patnaik, S.4
  • 28
  • 34
    • 0036644261 scopus 로고    scopus 로고
    • This stereochemical outcome is anticipated. For recent examples from these laboratories, see: (a) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841. (b) Williams, D. R.; Heiderbrecht, R. W., Jr. J. Am. Chem. Soc. 2003, 125, 1843.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4841
    • Williams, D.R.1    Mi, L.2    Mullins, R.J.3    Stites, R.E.4
  • 35
    • 0037442892 scopus 로고    scopus 로고
    • This stereochemical outcome is anticipated. For recent examples from these laboratories, see: (a) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841. (b) Williams, D. R.; Heiderbrecht, R. W., Jr. J. Am. Chem. Soc. 2003, 125, 1843.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1843
    • Williams, D.R.1    Heiderbrecht Jr., R.W.2
  • 38
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    • see ref 10
    • The stereochemistry of the major (17R)-diastereomer was confirmed by modified Mosher ester analysis (see ref 10).
  • 43
    • 0346017315 scopus 로고    scopus 로고
    • note
    • Yamaguchi conditions also led to small amounts (5-15%) of the [3.3.1]-bicyclic lactone i, which can be recycled to the seco-acid 23 via KOH, aqueous methanol. (Equation Presented)
  • 44
    • 0347908762 scopus 로고    scopus 로고
    • see ref 3b
    • 5 tetrahydropyranone; for direct comparison with a sample independently prepared from our first generation strategy, see ref 3b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.