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Volumn 122, Issue 38, 2000, Pages 9324-9325

First synthesis of a rearranged neo-clerodane diterpenoid. Development of totally regioselective trisubstituted furan ring assembly and medium-ring alkylation tactics for efficient access to (-)-teubrevin G [15]

Author keywords

[No Author keywords available]

Indexed keywords

CLERODANE DERIVATIVE; DITERPENOID; FURAN DERIVATIVE; TEUBREVIN G; UNCLASSIFIED DRUG;

EID: 0034721441     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002450x     Document Type: Letter
Times cited : (39)

References (35)
  • 3
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    • (b) Hanson, J. R. Nat. Prod. Rep. 1993, 10, 159; 1994, 11, 265.
    • (1994) Nat. Prod. Rep. , vol.11 , pp. 265
  • 8
    • 0342871111 scopus 로고    scopus 로고
    • note
    • The numbering is that originally proposed by Rodriguez et al. 3 and appears unusual because an attempt has been made to track the relocation of the carbon atoms during the ring-opening rearrangement.
  • 19
    • 0028276503 scopus 로고
    • and a 2,3,5-trisubstituted furan
    • This process appears to have been applied only once to construction of a 2,3,4- (Yadav, J. S.; Valluri, M.; Rao, A. V. R. Tetrahedron Lett. 1994, 35, 3609) and a 2,3,5-trisubstituted furan ( Iesce, M. R.; Cermola, F.; Graziano, M. L.; Scarpati, R. J. Chem. Soc., Perkin Trans. 1 1994, 147).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3609
    • Yadav, J.S.1    Valluri, M.2    Rao, A.V.R.3
  • 20
    • 37049073509 scopus 로고
    • This process appears to have been applied only once to construction of a 2,3,4- (Yadav, J. S.; Valluri, M.; Rao, A. V. R. Tetrahedron Lett. 1994, 35, 3609) and a 2,3,5-trisubstituted furan ( Iesce, M. R.; Cermola, F.; Graziano, M. L.; Scarpati, R. J. Chem. Soc., Perkin Trans. 1 1994, 147).
    • (1994) Chem. Soc., Perkin Trans. 1 , pp. 147
    • Iesce, M.R.1    Cermola, F.2    Graziano, M.L.3    Scarpati, R.J.4
  • 21
    • 0001466051 scopus 로고
    • Oxazole 8 was prepared by sequential reaction of the known acetal of methyl acetoacetate (Zamir, L. O.; Sauriol, F.; Nguen, C.-D. Tetrahedron Lett. 1987, 28, 3059. Chan, T. H.; Brook, M. A.; Chaly, T. Synthesis 1983, 203) with ammonium hydroxide and then with phenacyl bromide in toluene at 100 °C.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3059
    • Zamir, L.O.1    Sauriol, F.2    Nguen, C.-D.3
  • 22
    • 84988093935 scopus 로고
    • with ammonium hydroxide and then with phenacyl bromide in toluene at 100 °C
    • Oxazole 8 was prepared by sequential reaction of the known acetal of methyl acetoacetate (Zamir, L. O.; Sauriol, F.; Nguen, C.-D. Tetrahedron Lett. 1987, 28, 3059. Chan, T. H.; Brook, M. A.; Chaly, T. Synthesis 1983, 203) with ammonium hydroxide and then with phenacyl bromide in toluene at 100 °C.
    • (1983) Synthesis , pp. 203
    • Chan, T.H.1    Brook, M.A.2    Chaly, T.3
  • 27
    • 0033578944 scopus 로고    scopus 로고
    • and references therein
    • Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, 64, 7202 and references therein.
    • (1999) J. Org. Chem. , vol.64 , pp. 7202
    • Ulman, M.1    Grubbs, R.H.2
  • 34
    • 0033617277 scopus 로고    scopus 로고
    • The (2R)-diol of >90% ee was condensed with p-methoxybenzaldehyde dimethylacetal, reduced with Dibal-H, and exposed to triphenylphosphine diiodide
    • This reagent was prepared from 3-vinylfuran via asymmetric dihydroxylation by analogy to the 2-isomer (Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982). The (2R)-diol of >90% ee was condensed with p-methoxybenzaldehyde dimethylacetal, reduced with Dibal-H, and exposed to triphenylphosphine diiodide.
    • (1999) J. Org. Chem. , vol.64 , pp. 2982
    • Harris, J.M.1    Keranen, M.D.2    O'Doherty, G.A.3
  • 35
    • 0343306084 scopus 로고    scopus 로고
    • note
    • 3). 3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.