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1
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0000469856
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Audia J.E., Boisvert L., Patten A.D., Villalobos A., Danishefsky S.J. J. Org. Chem. 54:1989;3738-3740.
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(1989)
J. Org. Chem.
, vol.54
, pp. 3738-3740
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Audia, J.E.1
Boisvert, L.2
Patten, A.D.3
Villalobos, A.4
Danishefsky, S.J.5
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5
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0025092295
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Carreno M.C., Garcia Ruano J.L., Garrido M., Pilar Ruiz M., Solladie G. Tetrahedron Lett. 46:1990;6653.
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(1990)
Tetrahedron Lett.
, vol.46
, pp. 6653
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Carreno, M.C.1
Garcia Ruano, J.L.2
Garrido, M.3
Pilar Ruiz, M.4
Solladie, G.5
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7
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0342847839
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Both (R)- and (S)-limonene oxide is commercially available, normally at equal cost, allowing an effective means of preparing either enantiomer of 2a
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Both (R)- and (S)-limonene oxide is commercially available, normally at equal cost, allowing an effective means of preparing either enantiomer of 2a.
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10
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33748581378
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Chida N., Sugihara K., Amano S., Ogawa S. J. Chem. Soc., Perkin Trans. 1. 1997;275.
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(1997)
J. Chem. Soc., Perkin Trans. 1
, pp. 275
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Chida, N.1
Sugihara, K.2
Amano, S.3
Ogawa, S.4
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11
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33751392466
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Cane, D. E.; Yang, G.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454. No purifications are used in the synthesis of 4. Attempts to follow the Schreiber protocol, Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363-2366, of a one-pot conversion of an isopropenyl side-chain to an acetate invariably lead to large amounts of ketone with this substrate.
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(1992)
J. Org. Chem.
, vol.57
, pp. 3454
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Cane, D.E.1
Yang, G.2
Coates, R.M.3
Pyun, H.4
Hohn, T.M.5
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12
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0000083470
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No purifications are used in the synthesis of 4. Attempts to follow the Schreiber protocol, of a one-pot conversion of an isopropenyl side-chain to an acetate invariably lead to large amounts of ketone with this substrate
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Cane, D. E.; Yang, G.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454. No purifications are used in the synthesis of 4. Attempts to follow the Schreiber protocol, Schreiber, S. L.; Liew, W. F. Tetrahedron Lett. 1983, 24, 2363-2366, of a one-pot conversion of an isopropenyl side-chain to an acetate invariably lead to large amounts of ketone with this substrate.
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(1983)
Tetrahedron Lett.
, vol.24
, pp. 2363-2366
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Schreiber, S.L.1
Liew, W.F.2
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13
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33847805576
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Yasuda A., Tanaka S., Oshima K., Yamamoto H., Nozaki H. J. Am. Chem. Soc. 96:1974;6513.
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(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 6513
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Yasuda, A.1
Tanaka, S.2
Oshima, K.3
Yamamoto, H.4
Nozaki, H.5
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14
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0343282526
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Without careful removal of the palladium catalyst, distillation of the diene results in aromatization to toluene. However, 20 g of product can be filtered through 1/2 inch of silica, eluting with hexane.
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Without careful removal of the palladium catalyst, distillation of the diene results in aromatization to toluene. However, 20 g of product can be filtered through 1/2 inch of silica, eluting with hexane.
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16
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0024588558
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On a larger scale, 2a can be distilled (>90% purity by GC)
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On a larger scale, 2a can be distilled (>90% purity by GC). Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599.
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(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 2599
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Danishefsky, S.J.1
Simoneau, B.2
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17
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0343718026
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note
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4, and concentrated. Flash chromatography (4:1 hex-EtOAc) afforded 10.4 g (83%) of a clear colorless oil.
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18
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0343282528
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Racemic 2a was synthesized as a standard for HPLC analysis. The ee was determined by HPLC: ChiralCel OD 25 cm with 5 cm guard column (97:3, hexane:i-PrOH, 1 mL/min), (S)-enantiomer 6.1 min, (R)-enantiomer 6.7 min. (R)-Limonene oxide, purchased from Aldrich is reported as 98.5% ee.
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Racemic 2a was synthesized as a standard for HPLC analysis. The ee was determined by HPLC: ChiralCel OD 25 cm with 5 cm guard column (97:3, hexane:i-PrOH, 1 mL/min), (S)-enantiomer 6.1 min, (R)-enantiomer 6.7 min. (R)-Limonene oxide, purchased from Aldrich is reported as 98.5% ee.
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19
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0343718027
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Enone 2b was used in racemic form.
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Enone 2b was used in racemic form.
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21
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0342847838
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3 in contrast yields the complimentary 1,5-reduction adduct 12.
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3 in contrast yields the complimentary 1,5-reduction adduct 12.
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