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Volumn 49, Issue 8, 2008, Pages 1376-1379

Total synthesis of A-315675 based on the cascade Overman rearrangement

Author keywords

A 315675; Antiinfluenza agent; Cascade Overman rearrangement; Total synthesis

Indexed keywords

A 315675; ANTIVIRUS AGENT; PYRROLIDINE DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

EID: 38349140684     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.080     Document Type: Article
Times cited : (37)

References (37)
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    • Raja, S. N.; George, K. S. T.; Fan, L.; Nequist, G.; Reisch, T.; Maring, C.; McDaniel, K.; DeGoy, D.; Darbyshire, K. Abstracts of Papers, 41st Interscience Conference on Antimicrobial Agents and chemotherapy, Chicago, IL; American Society for Microbiology: Washington, DC, 2001; Abstract F-1683.
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    • Abed, Y.; Nehmé, B.; Baz, M.; Boivin, G. Antiviral Res., in press. doi:10.1016/j.antiviral.2007.08.008.
  • 9
    • 33646064214 scopus 로고    scopus 로고
    • For an excellent review on Overman rearrangement and related reactions, see:. Overman L.E. (Ed), Wiley, New York, NY
    • For an excellent review on Overman rearrangement and related reactions, see:. Overman L.E., and Carpenter N.E. In: Overman L.E. (Ed). Organic Reactions Vol. 66 (2005), Wiley, New York, NY 1-107
    • (2005) Organic Reactions , vol.66 , pp. 1-107
    • Overman, L.E.1    Carpenter, N.E.2
  • 10
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    • Recent representative reports on the Overman rearrangement and the related sigmatropic rearrangement of allylic secondary alcohols, see:
    • Recent representative reports on the Overman rearrangement and the related sigmatropic rearrangement of allylic secondary alcohols, see:. Savage I., Thomas E.J., and Wilson P.D. J. Chem. Soc., Perkin Trans. 1 (1999) 3291-3303
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 3291-3303
    • Savage, I.1    Thomas, E.J.2    Wilson, P.D.3
  • 16
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    • Report of the successful cascade Overman rearrangement on 1,2-dihydroxy-3-cyclohexene, see:
    • Report of the successful cascade Overman rearrangement on 1,2-dihydroxy-3-cyclohexene, see:. Demay S., Kotschy A., and Knochel P. Synthesis (2001) 863-866
    • (2001) Synthesis , pp. 863-866
    • Demay, S.1    Kotschy, A.2    Knochel, P.3
  • 17
    • 33846311745 scopus 로고    scopus 로고
    • Construction of diamines from allylic 1,2-diols by the stepwise sigmatropic rearrangement, see:
    • Construction of diamines from allylic 1,2-diols by the stepwise sigmatropic rearrangement, see:. Ichikawa Y., Egawa H., Ito T., Isobe M., Nakano K., and Kotsuki H. Org. Lett. 8 (2006) 5737-5740
    • (2006) Org. Lett. , vol.8 , pp. 5737-5740
    • Ichikawa, Y.1    Egawa, H.2    Ito, T.3    Isobe, M.4    Nakano, K.5    Kotsuki, H.6
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    • Ando K. Synlett (2001) 1272-1274
    • (2001) Synlett , pp. 1272-1274
    • Ando, K.1
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    • note
    • 13C NMR, IR and mass spectrometric and/or elemental analyses.
  • 24
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    • note
    • A similar reaction of the E-isomer of 9 with methylmagnesium bromide, in which the chelation of magnesium between the carbonyl and the dioxolane ring is geometrically impossible, produced a mixture (ca. 1.5:1) of tertiary alcohols.
  • 29
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    • note
    • It was found that in the Wittig reaction of 17, the reaction temperature is important for the high Z-selectivity. When the reaction was carried out at 0 °C, a mixture of the Z- and E-isomers (ca. 10:1) was obtained.
  • 31
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    • Some representative reports on the cascade sigmatropic rearrangement, see:
    • Some representative reports on the cascade sigmatropic rearrangement, see:. Thamos A.F. J. Am. Chem. Soc. 91 (1969) 3281-3283
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 3281-3283
    • Thamos, A.F.1
  • 37
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    • Recently, we have reported the synthesis of (-)-morphine utilizing the cascade Claisen rearrangement of a cyclohexene-diol derivative. See, Tanimoto, H.; Saito, R.; Chida, N. Tetrahedron Lett. 2008, 49, 358-362.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.