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Volumn 63, Issue 17, 1998, Pages 5742-5743

Synthesis of the chiral CD rings of paclitaxel from 2-deoxy-D-ribose: Novel 1,2-addition of a dienolate to a chiral ketone

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYRIBOSE; KETONE; PACLITAXEL;

EID: 0032555404     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9810563     Document Type: Article
Times cited : (17)

References (28)
  • 10
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    • note
    • Details of the calculations and those of other candidates are presented in the Supporting Information.
  • 11
    • 0141665638 scopus 로고
    • The α-preference regioselectivity observed in the aldol reaction of the dienolate of 3-methylcrotonate with a steroidal aldehyde has been reported. Kajikawa, A.; Morisaki, M.; Ikekawa, N. Tetrahedron Lett. 1975, 47, 4135.
    • (1975) Tetrahedron Lett. , vol.47 , pp. 4135
    • Kajikawa, A.1    Morisaki, M.2    Ikekawa, N.3
  • 12
    • 0000577782 scopus 로고
    • Preliminary stereochemical studies on the reactions of the dienolate of 3-methylcrotonate with aldehydes have been reported. Dugger, R. W.; Heathcock, C. H. J. Org. Chem. 1980, 45, 1181. Majewski, M.; Mpango, G. B.; Thomas, M. T.; Snieckus, V. J. Org. Chem. 1981, 46, 2029.
    • (1980) J. Org. Chem. , vol.45 , pp. 1181
    • Dugger, R.W.1    Heathcock, C.H.2
  • 13
    • 0000742701 scopus 로고
    • Preliminary stereochemical studies on the reactions of the dienolate of 3-methylcrotonate with aldehydes have been reported. Dugger, R. W.; Heathcock, C. H. J. Org. Chem. 1980, 45, 1181. Majewski, M.; Mpango, G. B.; Thomas, M. T.; Snieckus, V. J. Org. Chem. 1981, 46, 2029.
    • (1981) J. Org. Chem. , vol.46 , pp. 2029
    • Majewski, M.1    Mpango, G.B.2    Thomas, M.T.3    Snieckus, V.4
  • 14
    • 0030600169 scopus 로고    scopus 로고
    • For recent examples of stereocontrolled aldol reactions of a dienolate bearing a chiral auxiliary to aldehydes, see: Black, W. C.; Giroux, A.; Greidanus, G. Tetrahedron Lett. 1996, 37, 4471. Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1996, 37, 8899.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4471
    • Black, W.C.1    Giroux, A.2    Greidanus, G.3
  • 15
    • 0030566869 scopus 로고    scopus 로고
    • For recent examples of stereocontrolled aldol reactions of a dienolate bearing a chiral auxiliary to aldehydes, see: Black, W. C.; Giroux, A.; Greidanus, G. Tetrahedron Lett. 1996, 37, 4471. Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1996, 37, 8899.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8899
    • Tomooka, K.1    Nagasawa, A.2    Wei, S.-Y.3    Nakai, T.4
  • 16
    • 14444267395 scopus 로고    scopus 로고
    • note
    • 2-Deoxy-D-ribose was a gift from Kobayashi Koryo Kagaku.
  • 18
    • 14444283200 scopus 로고    scopus 로고
    • note
    • Acid hydrolysis, followed by reduction, gave the desired diol 9 in rather low yield because of β-elimination of the lactol.
  • 21
    • 14444276132 scopus 로고    scopus 로고
    • note
    • Addition of 1 equiv of the ester enolate of 5 gave a low yield (30%). This also suggests that the (E)-enolate is less reactive in the 1,2-addition.
  • 24
    • 0030721029 scopus 로고    scopus 로고
    • Compound i was also formed in 33% yield, probably from the regioisomeric product in the (3 + 2) cycloaddition. This regioselectivity has previously observed in the intramolecular (3 + 2) cycloaddition of N-substituted nitrones. Majumdar, S.; Bhattacharjya, A.; Patra, A. Tetrahedron Lett. 1997, 38, 8581. (Matrix Presented)
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8581
    • Majumdar, S.1    Bhattacharjya, A.2    Patra, A.3
  • 26
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    • Kozikowski, A. P.; Stein, P. D. J. Am. Chem. Soc. 1982, 104, 4023. Curran, D. P. J. Am. Chem. Soc. 1982, 104, 4024.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4024
    • Curran, D.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.