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Volumn 111, Issue 15, 1989, Pages 5810-5818

Fully Synthetic Stereoselective Routes to the Differentially Protected Subunits of the Tunicamycins

Author keywords

[No Author keywords available]

Indexed keywords

TUNICAMYCIN;

EID: 0024315358     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00197a047     Document Type: Article
Times cited : (77)

References (25)
  • 1
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    • Takatsuka, A.; Tamura, G. J. Chem. Phys. 1971, 24, 224. Takatsuka, A.; Tamura, G. J. Chem. Phys. 1971, 24, 232. Takatsuka, A.; Tamura, G. J. Chem. Phys. 1971, 24, 785.
    • Takatsuka, A.; Arimak, G. J. Antibiot. 1971, 24, 215. Takatsuka, A.; Tamura, G. J. Chem. Phys. 1971, 24, 224. Takatsuka, A.; Tamura, G. J. Chem. Phys. 1971, 24, 232. Takatsuka, A.; Tamura, G. J. Chem. Phys. 1971, 24, 785.
    • (1971) J. Antibiot , vol.24 , pp. 215
    • Takatsuka, A.1    Arimak, G.2
  • 6
    • 0013047363 scopus 로고
    • Japan Scientific Press: Tokyo
    • Tunicamycin; Japan Scientific Press: Tokyo, 1982.
    • (1982) Tunicamycin
  • 8
    • 0022358611 scopus 로고
    • For a preliminary communication describing the route from a methyl riboside derivative to peracetyltunicaminyluracil, see
    • For a preliminary communication describing the route from a methyl riboside derivative to peracetyltunicaminyluracil, see: Danishefsky, S.; Barbachyn, M. J. Am. Chem. Soc. 1985, 107, 7761.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 7761
    • Danishefsky, S.1    Barbachyn, M.2
  • 11
    • 0021127477 scopus 로고
    • Suami, T.; Sasai, H.; Matsuno, K.; Suzuki, N. Carbohydr. Res. 1985, 143, 85. In this work Suami uses the 3-propionate ester corresponding to the 3-OTBS ether of our fully synthetic material. We also were unable to couple the very same propionate substrate used by Suami.
    • Suami, T.; Sasai, H.; Matsun, K.; Suzuki, N.; Fukuda, Y.; Sakanaka, O. Tetrahedron Lett. 1984, 25, 4533. Suami, T.; Sasai, H.; Matsuno, K.; Suzuki, N. Carbohydr. Res. 1985, 143, 85. In this work Suami uses the 3-propionate ester corresponding to the 3-OTBS ether of our fully synthetic material. We also were unable to couple the very same propionate substrate used by Suami.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4533
    • Suami, T.1    Sasai, H.2    Matsun, K.3    Suzuki, N.4    Fukuda, Y.5    Sakanaka, O.6
  • 12
    • 0343892292 scopus 로고
    • For a recent disclosure with a similar trehalose coupling using similar substrates, see
    • For a recent disclosure with a similar trehalose coupling using similar substrates, see: Kominato, K.; Ogawa, S.; Suami, T. Carbohydr. Res. 1988, 174, 360.
    • (1988) Carbohydr. Res. , vol.174 , pp. 360
    • Kominato, K.1    Ogawa, S.2    Suami, T.3
  • 20
    • 33845471918 scopus 로고
    • For a previous preparation of a related aldehyde, see
    • For a previous preparation of a related aldehyde, see Corey, E. J.; Samuelson, B. J. Org. Chem. 1984, 49, 4735.
    • (1984) J. Org. Chem. , vol.49 , pp. 4735
    • Corey, E.J.1    Samuelson, B.2
  • 22
    • 0023688038 scopus 로고
    • For the formation of glycosides from azodicarboxylate-glycal cycloadducts, see
    • For the formation of glycosides from azodicarboxylate-glycal cycloadducts, see: Fitzsimmons, B. J.; Leblanc, Y.; Chan, N.; Rokach, J. J. Am. Chem. Soc. 1988, 110, 5229.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5229
    • Fitzsimmons, B.J.1    Leblanc, Y.2    Chan, N.3    Rokach, J.4
  • 24
    • 0010771837 scopus 로고
    • For an analysis of the stereochemical issues associated with Lewis acid induced addition of nucleophiles to aldehydes bearing proximate oxygens, see
    • For an analysis of the stereochemical issues associated with Lewis acid induced addition of nucleophiles to aldehydes bearing proximate oxygens, see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 556
    • Reetz, M.T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.