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For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
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Palomo, C.1
Aizpurua, J.M.2
Urchegi, R.3
García, J.M.4
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13
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0032871244
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For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
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Chem. Eur. J.
, vol.5
, pp. 2850-2858
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Schneider, C.1
Rehfeuter, M.2
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14
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0000575374
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For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
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Org. Lett.
, vol.2
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Trieselmann, T.1
Hoffmann, R.W.2
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15
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0034609699
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For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
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Org. Lett.
, vol.2
, pp. 3205-3208
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Sarraf, S.T.1
Leighton, J.L.2
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16
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0035940146
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-
See also ref 11b
-
For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
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Org. Lett.
, vol.3
, pp. 2777-2780
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Hunter, T.J.1
O'Doherty, G.A.2
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19
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0141603174
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-
note
-
Allylation under Keck and related conditions (ref 10) was unsuccessful here (extremely slow reaction). The use of the Duthaler-Hafner allylation reagent (ref 11) was discarded because of its very high price.
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-
-
-
20
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0001488391
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(a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
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J. Am. Chem. Soc.
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Keck, G.E.1
Tarbet, K.H.2
Geraci, L.S.3
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23
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0036402943
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(b) Cossy, J.; BouzBouz, S.; Pradaux, F.; Willis, C.; Bellosta, V. Synlett 2002, 1595-1606.
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Synlett
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Cossy, J.1
BouzBouz, S.2
Pradaux, F.3
Willis, C.4
Bellosta, V.5
-
24
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0141603173
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-
note
-
Freshly prepared by PCC oxidation of n-hexadecanol.
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-
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26
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0037000811
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(b) For a recent review on asymmetric allylborations, see: Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23-35.
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Aldrichimica Acta
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Ramachandran, P.V.1
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28
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0141714794
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note
-
Chomatographic separation of diastereomers (6 + epimer) proved to be unfeasible. After desilylation, separation was possible and the pure diol 7 was then resitylated to 8.
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-
-
-
29
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0001951357
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13C NMR and NOE measurements on the acetonide of diol 7. See: Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9-17.
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Acc. Chem. Res.
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Rychnovsky, S.D.1
Rogers, B.N.2
Richardson, T.I.3
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30
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0037131291
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Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547-7550.
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Ramachandran, P.V.1
Chandra, J.S.2
Reddy, M.V.R.3
-
31
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0141491538
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Basic desilylation reagent TBAF gives rise to lactone-opening reactions in this type of compound: Nakata, T.; Hata, N.; Oishi, T. Heterocycles 1990, 30, 333-334.
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(1990)
Heterocycles
, vol.30
, pp. 333-334
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Nakata, T.1
Hata, N.2
Oishi, T.3
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32
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0141714793
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note
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13C signals around 70 and 40 ppm.
-
-
-
-
33
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0024347403
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(5S,7R,9R,11R)-Stereoisomer, found in another plant source, is also different from passifloricin A. Its structure has been confirmed by stereoselective synthesis: Nakata, T.; Suenaga, T.; Nakashima, K.; Oishi, T. Tetrahedron Lett. 1989, 30, 6529-6532.
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(1989)
Tetrahedron Lett.
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Nakata, T.1
Suenaga, T.2
Nakashima, K.3
Oishi, T.4
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