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Uskokovic, M.R.1
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For the synthesis of biotin, see: (a) Chavan, S. P.; Chittiboyina, A. G.; Ramakrishna, G.; Tejwani, R. B.; Ravindranathan, T.; Kamat, S. K.; Rai, B.; Sivadasan, L.; Balkrishnan, K.; Ramalingam, S.; Deshpande, V. H. Tetrahedron 2005, 61, 9273.
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Chavan, S.P.1
Chittiboyina, A.G.2
Ramakrishna, G.3
Tejwani, R.B.4
Ravindranathan, T.5
Kamat, S.K.6
Rai, B.7
Sivadasan, L.8
Balkrishnan, K.9
Ramalingam, S.10
Deshpande, V.H.11
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3
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17144385857
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(b) Chen, F.E.; Chen, X.-X.; Dai, H.-F.; Kuang, Y.-Y.; Xie, B.; Zhao, J.-F. Adv. Synth. Catal. 2005, 347, 549.
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Chen, F.E.1
Chen, X.-X.2
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Kuang, Y.-Y.4
Xie, B.5
Zhao, J.-F.6
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5
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14544282389
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(d) Chavan, S. P.; Chittiboyina, A. G.; Ravindranathan, T.; Kamat, S. K.; Kalkota, U. R. J. Org. Chem. 2005, 70, 1901.
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Chavan, S.P.1
Chittiboyina, A.G.2
Ravindranathan, T.3
Kamat, S.K.4
Kalkota, U.R.5
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6
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4444284419
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(e) Chavan, S. P.; Ramakrishna, G.; Gonnade, R. G.; Bhadbhade, M. M. Tetrahedron Lett. 2004, 45, 7307.
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Chavan, S.P.1
Ramakrishna, G.2
Gonnade, R.G.3
Bhadbhade, M.M.4
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7
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34547945734
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(f) Seki, M.; Hatsuda, M.; Mori, Y.; Yoshida, S.; Yamada, S.; Shimizu, T. Chem. Eur. J. 2004, 10, 6101.
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Seki, M.1
Hatsuda, M.2
Mori, Y.3
Yoshida, S.4
Yamada, S.5
Shimizu, T.6
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10
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0345447575
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(i) Chen, F.-E.; Dai, H.-F.; Kuang, Y.-Y.; Jia, H.-Q. Tetrahedron: Asymmetry, 2003, 14, 3667.
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Chen, F.-E.1
Dai, H.-F.2
Kuang, Y.-Y.3
Jia, H.-Q.4
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(j) Seki, M.; Kimura, M.; Hatsuda, M.; Yoshida, S.; Shimizu. Tetrahedron Lett. 2003, 44, 8905.
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Kimura, M.2
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Yoshida, S.4
Shimizu5
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12
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0142057321
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(k) Chen, F.-E.; Yuan, J.-L.; Dai, H.-F.; Kuang, Y.-Y.; Chu, Y. Synthesis 2003, 2155.
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Chen, F.-E.1
Yuan, J.-L.2
Dai, H.-F.3
Kuang, Y.-Y.4
Chu, Y.5
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14
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0037047507
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(m) Seki, M.; Mori, Y.; Hatsuda, M.; Yamada, S. J. Org. Chem. 2002, 67, 5527.
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Seki, M.1
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Yamada, S.4
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17
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0037193142
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(p) Seki, M.; Hatsuda, M.; Mori, Y.; Yamada, S. Tetrahedron Lett. 2002, 43, 3269.
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0035823094
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(r) Chavan, S. P.; Tejwani, R. B.; Ravindranathan, T. J. Org. Chem. 2001, 66, 6197.
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Tejwani, R.B.2
Ravindranathan, T.3
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(u) Shimizu, M.; Nishigaki, Y.; Wakabayashi, A. Tetrahedron Lett. 1999, 40, 8873.
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Shimizu, M.1
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Wakabayashi, A.3
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24
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0001516297
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For a review on the synthesis of biotin, see:w
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For a review on the synthesis of biotin, see:(w) DeClercq, P. J. Chem. Rev. 1997, 97, 1755.
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Chem. Rev
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DeClercq, P.J.1
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23944485925
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(b) Nguyen, G. H.; Milea, J. S.; Rai, A.; Smith, C. L. Biomol. Eng. 2005, 22, 147.
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Milea, J.S.2
Rai, A.3
Smith, C.L.4
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28
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0038611015
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and references cited therein
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(d) de Boer, E.; Rodriguez, P.; Bonte, E.; Krijgsveld, J.; Katsantoni, E.; Heck, A.; Grosveld, F.; Strouboulis, J. Proc. Natl Acad. Sci. U.S.A. 2003, 100, 7480 and references cited therein.
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de Boer, E.1
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Katsantoni, E.5
Heck, A.6
Grosveld, F.7
Strouboulis, J.8
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29
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0026729616
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and reference cited therein
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Desarnaud, F.; Marie, J.; Larguier, R.; Lombard, C.; Jard, S.; Bonnafous, J.-C. J. Chromatogr. 1992, 603, 95 and reference cited therein.
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J. Chromatogr
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Desarnaud, F.1
Marie, J.2
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Lombard, C.4
Jard, S.5
Bonnafous, J.-C.6
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30
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0345168214
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For the relative avidin binding affinity of biotin and its metabolites, see: a
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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.
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(c) Finn, F. M.; Yamanouchi, K.; Titus, G.; Hofmann, K. Bioorg. Chem. 1995, 23, 152.
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Finn, F.M.1
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Titus, G.3
Hofmann, K.4
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35
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34547947171
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More detailed results will be published elsewhere
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More detailed results will be published elsewhere.
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36
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34547952364
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Low yield of the thiophene, presumably after dehydration, was obtained
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Low yield of the thiophene, presumably after dehydration, was obtained.
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37
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0000831711
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For intramolecular conjugate addition of carbamates, see: a
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For intramolecular conjugate addition of carbamates, see: (a) Wee, A. G. H.; McLeod, D. D.; Rankin, T. J. Heterocycles 1998, 48, 2263.
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Heterocycles
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Wee, A.G.H.1
McLeod, D.D.2
Rankin, T.J.3
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0030919222
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(b) Clayden, J.; Nelson, A.; Warren, S. Tetrahedron Lett. 1997, 38, 3471.
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Clayden, J.1
Nelson, A.2
Warren, S.3
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39
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0001011008
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(c) Hirama, M.; Hioki, H.; Ito, S.; Kabuto, C. Tetrahedron Lett. 1988, 29, 3121.
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Hirama, M.1
Hioki, H.2
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Kabuto, C.4
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(d) Hirama, M.; Hioki, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125.
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41
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34547962759
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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).
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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).
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42
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37049137716
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2866 the intramolecular conjugate addition of the carbamate from 3,4-bromohydrinsulfolane
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(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).
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(1972)
J. Chem. Soc., Perkin Trans. 1
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Ellis, F.1
Sammes, P.G.2
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43
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34547949055
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For the stereochemical assignment of hexahydrothienoimidazolone derivatives, see the Supporting Information
-
For the stereochemical assignment of hexahydrothienoimidazolone derivatives, see the Supporting Information.
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45
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33845374439
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Cere, V.; Paolucci, C.; Pollicino, S.; Sandri, E.; Fava, A. J. Org. Chem. 1986, 51, 4880.
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J. Org. Chem
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Cere, V.1
Paolucci, C.2
Pollicino, S.3
Sandri, E.4
Fava, A.5
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46
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0023571264
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Lee, H. L.; Baggiolini, E. G.; Uskokovic, M. R. Tetrahedron 1987, 43, 4887.
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Tetrahedron
, vol.43
, pp. 4887
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Lee, H.L.1
Baggiolini, E.G.2
Uskokovic, M.R.3
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47
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34547940587
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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.
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48
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34547929850
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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.
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-
-
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49
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34547934926
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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.
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