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Volumn 9, Issue 16, 2007, Pages 2973-2975

A rapid synthesis of the biotin core through a tandem michael reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BIOTIN; DRUG DERIVATIVE; SULFONE; SULFOXIDE; THIOPHENE DERIVATIVE; VINYL DERIVATIVE;

EID: 34547943518     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0710663     Document Type: Article
Times cited : (39)

References (49)
  • 1
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    • 3rd ed, Kirk, R. E, Othemr, D. E, Eds, Wiley: New York
    • Uskokovic, M. R. In Encyclopedia of Chemical Technology, 3rd ed.; Kirk, R. E., Othemr, D. E., Eds.; Wiley: New York, 1984; Vol. 24, p 41.
    • (1984) Encyclopedia of Chemical Technology , vol.24 , pp. 41
    • Uskokovic, M.R.1
  • 24
    • 0001516297 scopus 로고    scopus 로고
    • For a review on the synthesis of biotin, see:w
    • For a review on the synthesis of biotin, see:(w) DeClercq, P. J. Chem. Rev. 1997, 97, 1755.
    • (1997) Chem. Rev , vol.97 , pp. 1755
    • DeClercq, P.J.1
  • 30
    • 0345168214 scopus 로고    scopus 로고
    • For the relative avidin binding affinity of biotin and its metabolites, see: a
    • For the relative avidin binding affinity of biotin and its metabolites, see: (a) Sachon, E.; Tasseau, O.; Lavielle, S.; Sagan, S.; Bolbach, G. Anal. Chem. 2003, 75, 6536.
    • (2003) Anal. Chem , vol.75 , pp. 6536
    • Sachon, E.1    Tasseau, O.2    Lavielle, S.3    Sagan, S.4    Bolbach, G.5
  • 35
    • 34547947171 scopus 로고    scopus 로고
    • More detailed results will be published elsewhere
    • More detailed results will be published elsewhere.
  • 36
    • 34547952364 scopus 로고    scopus 로고
    • Low yield of the thiophene, presumably after dehydration, was obtained
    • Low yield of the thiophene, presumably after dehydration, was obtained.
  • 37
    • 0000831711 scopus 로고    scopus 로고
    • For intramolecular conjugate addition of carbamates, see: a
    • For intramolecular conjugate addition of carbamates, see: (a) Wee, A. G. H.; McLeod, D. D.; Rankin, T. J. Heterocycles 1998, 48, 2263.
    • (1998) Heterocycles , vol.48 , pp. 2263
    • Wee, A.G.H.1    McLeod, D.D.2    Rankin, T.J.3
  • 41
    • 34547962759 scopus 로고    scopus 로고
    • For the synthesis of N,N′-dibenzyl-cis-ureylenesulfone from 2,5-dihydrothiophene S,S-dioxide, see: (a) Kotake, H.; Inomata, K.; Murata, Y.; Kinoshita, H.; Katsuragana, M. Chem. Lett. 1976, 1073 (the reaction of 3,4-dibromosulfolane with benzylamine).
    • For the synthesis of N,N′-dibenzyl-cis-ureylenesulfone from 2,5-dihydrothiophene S,S-dioxide, see: (a) Kotake, H.; Inomata, K.; Murata, Y.; Kinoshita, H.; Katsuragana, M. Chem. Lett. 1976, 1073 (the reaction of 3,4-dibromosulfolane with benzylamine).
  • 42
    • 37049137716 scopus 로고
    • 2866 the intramolecular conjugate addition of the carbamate from 3,4-bromohydrinsulfolane
    • (b) Ellis, F.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1972, 2866 (the intramolecular conjugate addition of the carbamate from 3,4-bromohydrinsulfolane).
    • (1972) J. Chem. Soc., Perkin Trans. 1
    • Ellis, F.1    Sammes, P.G.2
  • 43
    • 34547949055 scopus 로고    scopus 로고
    • For the stereochemical assignment of hexahydrothienoimidazolone derivatives, see the Supporting Information
    • For the stereochemical assignment of hexahydrothienoimidazolone derivatives, see the Supporting Information.
  • 47
    • 34547940587 scopus 로고    scopus 로고
    • Sulfone 3 can be obtained through oxidation of biotin derivative 18, see ref 5
    • Sulfone 3 can be obtained through oxidation of biotin derivative 18, see ref 5.
  • 48
    • 34547929850 scopus 로고    scopus 로고
    • The sulfoxide 17 does not epimerize under identical conditions, the stereoselectivity of 6 was derived from the sulfoxide 16 (2,3-trans:2,3-cis = 3:2), see the Supporting Information.
    • The sulfoxide 17 does not epimerize under identical conditions, the stereoselectivity of 6 was derived from the sulfoxide 16 (2,3-trans:2,3-cis = 3:2), see the Supporting Information.
  • 49
    • 34547934926 scopus 로고    scopus 로고
    • Treatment with LDA at -78°C then tert-butanol quenching led to decomposion as well as the recovery of the starting material.
    • Treatment with LDA at -78°C then tert-butanol quenching led to decomposion as well as the recovery of the starting material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.