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(1) (a) Adamczeski, M.; Quiñoà, E.; Crews, P. J. Am. Chem. Soc. 1988, 110, 1598-1602;
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Adamczeski, M.1
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2
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0029953345
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(b) Searle, P. A.; Richter, R. K.; Molinski, T. F. J. Org. Chem. 1996, 61, 4073-4079;
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Searle, P.A.1
Richter, R.K.2
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3
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0027761764
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(c) Rodríguez, J.; Nieto, R. M.; Crews, P. J. Nat. Prod. 1993, 56, 2034-2040;
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Rodríguez, J.1
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4
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0027937370
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(d) Rudi, A.; Kashman, Y.; Benayahu, Y.; Schleyer, M. J. Nat. Prod. 1994, 57, 829-832.
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Rudi, A.1
Kashman, Y.2
Benayahu, Y.3
Schleyer, M.4
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6
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0010559519
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unpublished results
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(b) Minimum inhibitory concentration (MIC) against C. albicans (ATCC 14503) and certain Fluconazole® resistant strains is ∼ 1μg/ml, Molinski, T.F. et al., unpublished results.
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Molinski, T.F.1
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7
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0027050190
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hennoxazole
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(3) Most published syntheses of natural products bearing 2,4-disubstituted oxazole employ the serine amide cyclodehydration-oxidation methodology. Recent examples include total syntheses of calyculin A, (a) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453; hennoxazole,
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J. Am. Chem. Soc.
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Evans, D.A.1
Gage, J.R.2
Leighton, J.L.3
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9
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0001620021
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rhizoxin
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(c) Wipf, P.; Lim, S. Chimia 1996, 50, 157-167; rhizoxin,
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(1996)
Chimia
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Wipf, P.1
Lim, S.2
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10
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0027480114
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(d) Nakada, M.; Kobayashi, S.; Iwasaki, S.; Ohno, M. Tetrahedron Lett. 1993, 34, 1035-1038,
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Tetrahedron Lett.
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Nakada, M.1
Kobayashi, S.2
Iwasaki, S.3
Ohno, M.4
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11
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0027535385
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(e) Nakada, M.; Kobayashi, S.; Shibasaki, M.; Iwasaki, S.; Ohno, M. Tetrahedron Lett. 1993, 34, 1039-1042,
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Tetrahedron Lett.
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Nakada, M.1
Kobayashi, S.2
Shibasaki, M.3
Iwasaki, S.4
Ohno, M.5
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12
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0030839481
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(f) Williams, D. R.; Werner, K. M.; Feng, B. N. Tetrahedron Lett. 1997, 38, 6825-6828, and the trisoxazole segment of the halichondramide macrolide family,
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Tetrahedron Lett.
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Williams, D.R.1
Werner, K.M.2
Feng, B.N.3
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13
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85034351889
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(g) Knight, D.W.; Pattenden, G.; Rippon, D.E. Synlett, 1990, 1, 36. Useful alternatives to the serine amide motiff can be seen in the 'aziridine approach', eg.
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(1990)
Synlett
, vol.1
, pp. 36
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Knight, D.W.1
Pattenden, G.2
Rippon, D.E.3
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14
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0028260089
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(h) Eastwood, F. W.; Perlmutter, P.; Qi, Y. Tetrahedron Lett. 1994, 35, 2039-2042 and
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(1994)
Tetrahedron Lett.
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Eastwood, F.W.1
Perlmutter, P.2
Qi, Y.3
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17
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0000747989
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(4) Hodges, J. C.; Patt, W. C.; Connolly, C. J. J. Org. Chem. 1991, 56, 449-452 and citations, within. Coupling of 4 with a variety of aldehydes occurs exclusively at C-4 in 20-65% yield.
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J. Org. Chem.
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Hodges, J.C.1
Patt, W.C.2
Connolly, C.J.3
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19
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0010621869
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note
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13C NMR spectra, and elemental analysis or HRMS.
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20
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0001230834
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(6) Catelani, G.; Colonna, F.; Marra, A. Carbohydr. Res. 1988, 182, 297-300.
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(1988)
Carbohydr. Res.
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Catelani, G.1
Colonna, F.2
Marra, A.3
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21
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0025184665
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(7) Hanessian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276-5290.
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(1990)
J. Am. Chem. Soc.
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Hanessian, S.1
Cooke, N.G.2
DeHoff, B.3
Sakito, Y.4
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22
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33751385486
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(8) Barton, D. H.; Jang, D. O.; Jaszberenyi, J. C. J. Org. Chem. 1993, 58, 6838-6842.
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Barton, D.H.1
Jang, D.O.2
Jaszberenyi, J.C.3
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23
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0010621870
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note
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4HCOO-MeOH) was sluggish (>4 days) and gave mixtures with incomplete reaction or over-reducted alditol 9. Pretreating the substrate to remove trace sulfur impurities (Ra-Ni, EtOH, reflux) was only partially successful in improving the yield of 8.
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24
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0028294579
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5a See Kigoshi, K.; Ojika, M.; Suenaga, K.; Mutou, T.; Hirano, J.; Sakakura, A.; Ogawa, T.; Nisiwaki, M.; Yamada, K. Tetrahedron Lett. 1994, 35, 1247-1250 for application to a primary O-Bn ether.
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(1994)
Tetrahedron Lett.
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Kigoshi, K.1
Ojika, M.2
Suenaga, K.3
Mutou, T.4
Hirano, J.5
Sakakura, A.6
Ogawa, T.7
Nisiwaki, M.8
Yamada, K.9
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25
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0010590981
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note
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(11) The addition of phenyllithium to ent-8 proceeded in 86% yield and 1:2.4 diastereoselectivity in favor of the desired 6R epimer (bengazole numbering). See Ref. 1b.
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26
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0010559377
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note
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5Si requires 372.2206.
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27
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0001498230
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(13) The modest yield appears to be due, in part, to lower reactivity of 2-lithiooxazole compared to PhLi (see note 11) and competing enolization of 3 and β-elimination. Addition of 1.5 equiv of 2-lithiooxazole to 3 gave only ∼ 7% yield of 2. We are addressing this problem by modifying the preformed 2-lithiooxazole (enolate) prior to addition of 3, however other reaction pathways may be operative, see Iddon, B. Heterocydes 1994, 37, 1321-1346.
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(1994)
Heterocydes
, vol.37
, pp. 1321-1346
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Iddon, B.1
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28
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0004204440
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Turchi, I. J., Ed.
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(14) Turchi, I. J. In Oxazoles; Turchi, I. J., Ed.; The Chemistry of Heterocyclic Compounds, John Wiley & Sons: New York, 1986; Vol. 45; pp 1-341.
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Oxazoles
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Turchi, I.J.1
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29
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0010559378
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John Wiley & Sons: New York
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(14) Turchi, I. J. In Oxazoles; Turchi, I. J., Ed.; The Chemistry of Heterocyclic Compounds, John Wiley & Sons: New York, 1986; Vol. 45; pp 1-341.
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(1986)
The Chemistry of Heterocyclic Compounds
, vol.45
, pp. 1-341
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30
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0000858597
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(15) Vedejs, E.; Monahan, S. D. J. Org. Chem. 1996, 61, 5192-5193. The exception is oxazole-4-carboxylate derivatives which deprotonate and add electrophiles at C-5, exclusively.
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(1996)
J. Org. Chem.
, vol.61
, pp. 5192-5193
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Vedejs, E.1
Monahan, S.D.2
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