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Volumn 51, Issue 23, 2010, Pages 3053-3056

Syntheses of carbocyclic aminonucleosides and (-)-epi-4′-carbocyclic puromycin: application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations

Author keywords

[No Author keywords available]

Indexed keywords

AMINONUCLEOSIDE; CARBOCYCLIC NUCLEOSIDE; INDIUM; IODIDE; PALLADIUM; PUROMYCIN AMINONUCLEOSIDE;

EID: 77953123335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.006     Document Type: Article
Times cited : (10)

References (46)
  • 6
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    • Gottlieb D., and Shaw P.D. (Eds), Springer, New York
    • Nathans D. In: Gottlieb D., and Shaw P.D. (Eds). Antibiotics Vol. 1 (1967), Springer, New York 259-277
    • (1967) Antibiotics , vol.1 , pp. 259-277
    • Nathans, D.1
  • 28
    • 77953120866 scopus 로고    scopus 로고
    • note
    • 4 in the presence of t-BuOCl and NaOH. The substrate was not compatible with the harsh oxidizing conditions and a complex product mixture resulted within 10 min; compound (±)-9a was not observed by this method.
  • 29
    • 0037032268 scopus 로고    scopus 로고
    • For tethered aminohydroxylations with allyl carbamates as substrates, see:
    • For tethered aminohydroxylations with allyl carbamates as substrates, see:. Donohoe T.J., Johnson P.D., Cowley A., and Keenan M. J. Am. Chem. Soc. 124 (2002) 12934-12935
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12934-12935
    • Donohoe, T.J.1    Johnson, P.D.2    Cowley, A.3    Keenan, M.4
  • 31
    • 4143087960 scopus 로고    scopus 로고
    • For tethered amino-hydroxylations with homoallyl carbamates as substrates, see:
    • For tethered amino-hydroxylations with homoallyl carbamates as substrates, see:. Kenworthy M.N., McAllister G.D., and Taylor R.J.K. Tetrahedron Lett. 45 (2004) 6661-6664
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6661-6664
    • Kenworthy, M.N.1    McAllister, G.D.2    Taylor, R.J.K.3
  • 36
    • 77953123610 scopus 로고    scopus 로고
    • note
    • Attempts to directly prepare N-hydroxycarbamate (±)-7a from (±)-5a occurred with limited success. When homoallylic alcohol (±)-5a was stirred with CDI for 2 h and then treated with a solution of hydroxylamine hydrochloride and triethylamine, starting material (±)-5a was recovered and low conversion to N-hydroxycarbamate (±)-7a was observed.
  • 38
    • 84982367300 scopus 로고
    • a <7 for the NH of O-acylhydroxamic acids, see:
    • a <7 for the NH of O-acylhydroxamic acids, see:. Bauer L., and Exner O. Angew. Chem., Int. Ed. Engl. 13 (1974) 376-385
    • (1974) Angew. Chem., Int. Ed. Engl. , vol.13 , pp. 376-385
    • Bauer, L.1    Exner, O.2
  • 39
    • 77953120777 scopus 로고    scopus 로고
    • note
    • LC-MS of the crude reaction mixture indicated that (±)-8a was the major component of the reaction mixture (74%). Unreacted (±)-7a (16%), N-mono-benzolylated product (3%), and bis-benzolylated product (7%) were also present.
  • 41
    • 0001376012 scopus 로고    scopus 로고
    • Diastereofacial addition will be directed anti to the electron rich bonds that stabilize the developing antibonding orbitals in the transition state, see:
    • Diastereofacial addition will be directed anti to the electron rich bonds that stabilize the developing antibonding orbitals in the transition state, see:. Cieplak A.S. Chem. Rev. 99 (1999) 1265-1336
    • (1999) Chem. Rev. , vol.99 , pp. 1265-1336
    • Cieplak, A.S.1
  • 43
    • 77953121585 scopus 로고    scopus 로고
    • note
    • Carbamates have been observed as by-products in tethered aminohydroxylations, see: Ref. 13b, footnote 7.
  • 44
    • 77953122628 scopus 로고    scopus 로고
    • note
    • An imidotrioxoosmium (VII) species is proposed in the tethered aminohydroxylation reaction mechanism, see: Ref. 16b.
  • 46
    • 77953120495 scopus 로고    scopus 로고
    • note
    • Refer to Supplementary data for complete carbon and proton assignments for (±)-9a and (-)-9b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.