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Volumn 63, Issue 26, 1998, Pages 9624-9625

Enantioselective total synthesis of taurospongin A

Author keywords

[No Author keywords available]

Indexed keywords

DNA DIRECTED DNA POLYMERASE BETA; FATTY ACID DERIVATIVE; NATURAL PRODUCT; RNA DIRECTED DNA POLYMERASE INHIBITOR; TAURINE;

EID: 0032567320     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9819741     Document Type: Article
Times cited : (68)

References (22)
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    • note
    • Racemic epoxide 5 was prepared in two steps and 85% yield from commercially available 3-methyl-3-buten-1-ol (see the Supporting Information).
  • 7
    • 0032576854 scopus 로고    scopus 로고
    • For selected examples of kinetic resolution of 2,2-disubstituted epoxides, see: (a) Orru, R. V. A.; Mayer, S. F.; Kroutil, W.; Faber, K. Tetrahedron 1998, 54, 859-874. (b) Osprian, I.; Kroutil, W.; Mischitz, M.; Faber, K. Tetrahedron: Asymmetry 1997, 8, 65-71. (c) Lakner, F. J.; Hager, L. P. J. Org. Chem. 1996, 61, 3923-3925.
    • (1998) Tetrahedron , vol.54 , pp. 859-874
    • Orru, R.V.A.1    Mayer, S.F.2    Kroutil, W.3    Faber, K.4
  • 8
    • 0031016293 scopus 로고    scopus 로고
    • For selected examples of kinetic resolution of 2,2-disubstituted epoxides, see: (a) Orru, R. V. A.; Mayer, S. F.; Kroutil, W.; Faber, K. Tetrahedron 1998, 54, 859-874. (b) Osprian, I.; Kroutil, W.; Mischitz, M.; Faber, K. Tetrahedron: Asymmetry 1997, 8, 65-71. (c) Lakner, F. J.; Hager, L. P. J. Org. Chem. 1996, 61, 3923-3925.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 65-71
    • Osprian, I.1    Kroutil, W.2    Mischitz, M.3    Faber, K.4
  • 9
    • 0029941844 scopus 로고    scopus 로고
    • For selected examples of kinetic resolution of 2,2-disubstituted epoxides, see: (a) Orru, R. V. A.; Mayer, S. F.; Kroutil, W.; Faber, K. Tetrahedron 1998, 54, 859-874. (b) Osprian, I.; Kroutil, W.; Mischitz, M.; Faber, K. Tetrahedron: Asymmetry 1997, 8, 65-71. (c) Lakner, F. J.; Hager, L. P. J. Org. Chem. 1996, 61, 3923-3925.
    • (1996) J. Org. Chem. , vol.61 , pp. 3923-3925
    • Lakner, F.J.1    Hager, L.P.2
  • 10
    • 0001384657 scopus 로고
    • The stereochemical assignment was made by comparison with literature data: Gill, M.; Smrdel, A. F. Tetrahedron: Asymmetry 1990, 1, 453-464.
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 453-464
    • Gill, M.1    Smrdel, A.F.2
  • 15
    • 20644440685 scopus 로고    scopus 로고
    • note
    • The starting terminal alkyne 9 was also recovered in 24% yield.
  • 16
    • 0001164834 scopus 로고
    • For selected examples of diastereoselective reduction of β-alkoxy ketones to give syn-1,3-monoprotected diols, see: (a) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (b) Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396-1408. (c) Yoshimatsu, M.; Naito, M.; Shimizu, H.; Muraoka, O.; Tanabe, G.; Kataoka, T. J. Org. Chem. 1996, 61, 8200-8206.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5419-5422
    • Mori, Y.1    Kuhara, M.2    Takeuchi, A.3    Suzuki, M.4
  • 17
    • 0000346930 scopus 로고
    • For selected examples of diastereoselective reduction of β-alkoxy ketones to give syn-1,3-monoprotected diols, see: (a) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (b) Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396-1408. (c) Yoshimatsu, M.; Naito, M.; Shimizu, H.; Muraoka, O.; Tanabe, G.; Kataoka, T. J. Org. Chem. 1996, 61, 8200-8206.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1396-1408
    • Yamazaki, N.1    Kibayashi, C.2
  • 18
    • 0029824648 scopus 로고    scopus 로고
    • For selected examples of diastereoselective reduction of β-alkoxy ketones to give syn-1,3-monoprotected diols, see: (a) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422. (b) Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396-1408. (c) Yoshimatsu, M.; Naito, M.; Shimizu, H.; Muraoka, O.; Tanabe, G.; Kataoka, T. J. Org. Chem. 1996, 61, 8200-8206.
    • (1996) J. Org. Chem. , vol.61 , pp. 8200-8206
    • Yoshimatsu, M.1    Naito, M.2    Shimizu, H.3    Muraoka, O.4    Tanabe, G.5    Kataoka, T.6
  • 20
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    • note
    • 1H NMR spectrum. Both diastereoisomers were separable by flash chromatography.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.