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0041794668
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note
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To the best of our knowledge, lactones 1 and 2 have not been named; thus for simplicity reasons we will refer to 1 as cryptocarya diacetate and 2 as cryptocarya triacetate.
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4
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0032869162
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8
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0042796827
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note
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The Aldrich Chemical Co. provides (S)-tert-butyl 3-hydroxybutyrate at the cost of $41/mL.
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11
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0034639734
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For some recent approaches to related 6-substituted 5,6-dihydropyran-2-one containing natural products, see: (a) Gosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006.
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(c) Reddy, M. V. R.; Rearick, J. P.; Hoch, N.; Ramachandran, P. V. Org. Lett. 2001, 3, 19-20.
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17
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0001290552
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For other approaches to syn-3,5-dihydroxy carboxylic esters, see: (a) Miyazawa, M.; Matsuoka, E.; Sasaki, S.; Oonuma, S.; Maruyam, K. Miyashita, M. Chem. Lett. 1998, 109-110.
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(b) Evans, D. A.; Trotter, B. W.; Coleman, P. J.; Cote, B.; Dias, L. C.; Rajpakse, H. A.; Tyler, A. N. Tetrahedron 1999, 55, 8671-8726.
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Leighton has demonstrated that this can be accomplished by the addition of allyl-(-)-diisopinocamphenylborane to similarly protected aldehydes, but we hoped to find a less expensive alternative. Hornberger, K. R.; Hamblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894.
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0028071712
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The syn-1,3-diol structural unit is a common motif in many natural products, with a wide range of biological activities. (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765.
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24
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0041294096
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note
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The Aldrich Chemical Co. sells ethyl sorbate for $0.30/g.
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25
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33947086629
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All levels of enantioinduction were determined by HPLC analysis (8% IPA/hexane, Chiralcel OD) and/or Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
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0001384141
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(b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
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27
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0041294097
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note
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13C NMR, FTIR, and HRMS.
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(b) Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107-110.
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0042295801
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note
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This lower than normal (2:1 phosphine to palladium) ratio gave higher yields and faster reaction times.
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32
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0041294098
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note
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Others have noted low yields for similar acylations with acryloyl chloride, see ref 10e.
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33
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0032580376
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For a excellent review on ring closing metathesis reactions, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
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Chang, S.2
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0035850265
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For other uses of ring closing metathesis reactions for the formation of pyranones, see: ref 10a,b,e and Cossy, J.; Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235.
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