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1
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4243794106
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Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
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(1992)
Chem. Rev.
, vol.92
, pp. 1071
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Santaniello, E.1
Ferraboschi, P.2
Grisenti, P.3
Manzocchi, A.4
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2
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0026521033
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Grisenti, P.; Ferraboschi, P.; Manzocchi, A.; Santaniello, E. Tetrahedron 1992, 48, 3827.
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(1992)
Tetrahedron
, vol.48
, pp. 3827
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Grisenti, P.1
Ferraboschi, P.2
Manzocchi, A.3
Santaniello, E.4
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3
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0027955006
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Ferraboschi, P.; Casati, S.; Santaniello, E. Tetrahedron: Asymmetry 1994, 5, 19.
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(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 19
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Ferraboschi, P.1
Casati, S.2
Santaniello, E.3
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4
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1542678493
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note
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We also carried out an alternative synthesis of the silyl ether 3b starting from commercially available glycerol acetonide. This relatively trivial approch was quite satisfactory and proceeded in 4 steps with 35% yield. We decided to explore also the relatively new and more intriguing elaboration of DHAD that holds promises of future developments.
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5
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0009553174
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Cesarotti, E.; Antognazza, P.; Pallavicini, M.; Villa, L. Helv. Chim. Acta 1993, 76, 2344.
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(1993)
Helv. Chim. Acta
, vol.76
, pp. 2344
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Cesarotti, E.1
Antognazza, P.2
Pallavicini, M.3
Villa, L.4
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6
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0017889042
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For instance, the DHA monoacetate is long known and its preparation (30% yield) requires careful experimental conditions; see: Gettys, G. A.; Gutsche, C. D. Bioorg. Chem. 1978, 7, 141.
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(1978)
Bioorg. Chem.
, vol.7
, pp. 141
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Gettys, G.A.1
Gutsche, C.D.2
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7
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84987536369
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Aragozzini, F.; Maconi, E.; Potenza, D.; Scolastico, C. Synthesis 1989, 225
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(1989)
Synthesis
, pp. 225
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Aragozzini, F.1
Maconi, E.2
Potenza, D.3
Scolastico, C.4
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8
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1542783847
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note
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We were able to prepare the monoester 4b by controlled esterification of DHA or hydrolysis of the dibenzoate 4c, thus lowering the yield of the process.
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9
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1542468995
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note
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The selective preparation of a monosilyl ether of 4a would allow the preparation of the compound 3b as an intermediate of the benzyl ether 2a. However, the monosilylation of 4a as well as the hydrolysis of 4d to a monosilyl derivative were unsatisfactory.
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10
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0000491298
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Ogilvie, K. K.; Schifman, A. L.; Penney, C. L. Can. J. Chem. 1979, 57, 2230.
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(1979)
Can. J. Chem.
, vol.57
, pp. 2230
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Ogilvie, K.K.1
Schifman, A.L.2
Penney, C.L.3
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11
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49149146669
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Metcalf, B., W.; Burkhart, J. P.; Jund, K. W Tetrahedron. Lett. 1980, 21, 35.
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(1980)
Tetrahedron. Lett.
, vol.21
, pp. 35
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Metcalf, B.W.1
Burkhart, J.P.2
Jund, K.W.3
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12
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1542573561
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note
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2=C), 7.40-7.60 (m, 5 H, Ar).
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14
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0001083073
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Jung, S. -H.; Jeong, J -H, Miller, P.; Wong, C. -H. J. Org. Chem. 1994, 59, 7182.
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(1994)
J. Org. Chem.
, vol.59
, pp. 7182
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Jung, S.H.1
Jeong, J.H.2
Miller, P.3
Wong, C.H.4
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15
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0000872120
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Colbran, R. L.; Jones, J. K. N.; Matheson, N. K., Rozema, I. Carbohydr. Res. 1967, 4, 355.
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(1967)
Carbohydr. Res.
, vol.4
, pp. 355
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Colbran, R.L.1
Jones, J.K.N.2
Matheson, N.K.3
Rozema, I.4
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17
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0026073636
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Pederson, R. L.; Esker, J.; Wong, C. -H. Tetrahedron 1991, 47, 2643.
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(1991)
Tetrahedron
, vol.47
, pp. 2643
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Pederson, R.L.1
Esker, J.2
Wong, C.H.3
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18
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0028067680
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Compound 7c is obtained as a mixture of cis- and trans-isomers that could be separated by column chromatography. Similarly, it has been possible to isolate the single isomers of acetal 7b and determine their structure by X-ray chrystallography (Waagen, V.; Barua, T. K.; Anthonsen, H. W.; Hansen, L. K.; Fossli, D.-J.; Hough, E.; Anthonsen, T. Tetrahedron 1994, 50, 10055). For the next hydrolytic step, however, the isomeric mixture of 7c was directly used as such.
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(1994)
Tetrahedron
, vol.50
, pp. 10055
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Waagen, V.1
Barua, T.K.2
Anthonsen, H.W.3
Hansen, L.K.4
Fossli, D.-J.5
Hough, E.6
Anthonsen, T.7
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19
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1542468994
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note
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2O), 7.30-7.60 (m, 5 H, Ar).
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20
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1542468997
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note
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D +2.95 (c 2.2 in ethanol). The chemico-physical properties are as reported in the Ref. 2.
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21
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1542573560
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note
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When the incubation was carried out for a longer time (21 days) we isolated also (2R)-3-benzyloxy-2-methyl-propanoic acid. The configuration and enantiomeric excess (96%) of this compound was established by its reduction to the optically pure (25)-alcohol.
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22
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1542678492
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note
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2OCO appeared as three groups of signals at 4.23-4.27, 4.27-4.34 and 4.34-4.39 ppm (1:2:1 ratio) in the racemic compound. In the spectrum of the optically active 1a the signals betwen 4.27 and 4.34 ppm were not detectable.
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