-
1
-
-
0037700759
-
-
Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Zanardi, F.; Battistini, L.; Gaetani, E.; Curti, C.; Casiraghi, G. J. Org. Chem. 2003, 68, 5881-5885.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 5881-5885
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Zanardi, F.5
Battistini, L.6
Gaetani, E.7
Curti, C.8
Casiraghi, G.9
-
2
-
-
0034678033
-
-
For recent reviews on diversity-oriented synthesis, see: (a) Schreiber, S. L. Science 2000, 287, 1964-1969.
-
(2000)
Science
, vol.287
, pp. 1964-1969
-
-
Schreiber, S.L.1
-
3
-
-
0142147275
-
-
(b) Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613-618.
-
(2003)
Science
, vol.302
, pp. 613-618
-
-
Burke, M.D.1
Berger, E.M.2
Schreiber, S.L.3
-
4
-
-
77957047686
-
-
Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, The Netherlands
-
For recent reviews on carbasugars and relatives, see: (a) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Curti, C. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, The Netherlands, 2003; Vol. 29, pp 449-520.
-
(2003)
Studies in Natural Products Chemistry
, vol.29
, pp. 449-520
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Battistini, L.4
Curti, C.5
-
5
-
-
0033097654
-
-
(b) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779-844.
-
(1999)
Chem. Rev.
, vol.99
, pp. 779-844
-
-
Berecibar, A.1
Grandjean, C.2
Siriwardena, A.3
-
6
-
-
0000460802
-
-
(c) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195-1220.
-
(1996)
Chem. Rev.
, vol.96
, pp. 1195-1220
-
-
Hudlicky, T.1
Entwistle, D.A.2
Pitzer, K.K.3
Thorpe, A.J.4
-
7
-
-
0034613357
-
-
(a) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 6307-6318.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6307-6318
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Battistini, L.4
Zanardi, F.5
Marzocchi, L.6
Acquotti, D.7
Casiraghi, G.8
-
8
-
-
0035977220
-
-
(b) Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Battistini, L.; Zanardi, F.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2001, 66, 8070-8075.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8070-8075
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Battistini, L.5
Zanardi, F.6
Marzocchi, L.7
Acquotti, D.8
Casiraghi, G.9
-
9
-
-
0036087845
-
-
(c) Zanardi, F.; Battistini, L.; Marzocchi, L.; Acquotti, D.; Rassu, G.; Pinna, L.; Auzzas, L.; Zambrano, V.; Casiraghi, G. Eur. J. Org. Chem. 2002, 1956-1964.
-
(2002)
Eur. J. Org. Chem.
, pp. 1956-1964
-
-
Zanardi, F.1
Battistini, L.2
Marzocchi, L.3
Acquotti, D.4
Rassu, G.5
Pinna, L.6
Auzzas, L.7
Zambrano, V.8
Casiraghi, G.9
-
10
-
-
0037178533
-
-
(d) Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Zanardi, F.; Battistini, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2002, 67, 5338-5342.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 5338-5342
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Zanardi, F.5
Battistini, L.6
Marzocchi, L.7
Acquotti, D.8
Casiraghi, G.9
-
12
-
-
0037033210
-
-
(b) Mehta, G.; Lakshminath, S.; Talukdar, P. Tetrahedron Lett. 2002, 43, 335-338.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 335-338
-
-
Mehta, G.1
Lakshminath, S.2
Talukdar, P.3
-
13
-
-
0026771552
-
-
(c) Miyamoto, M.; Baker, M. L.; Lewis, M. D. Tetrahedron Lett. 1992, 33, 3725-3728.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 3725-3728
-
-
Miyamoto, M.1
Baker, M.L.2
Lewis, M.D.3
-
14
-
-
0027257084
-
-
(d) Augy-Dorey, S.; Dalko, P.; Géro, S. D.; Quiclet-Sire, B.; Eustache, J.; Stütz, P. Tetrahedron 1993, 49, 7997-8006.
-
(1993)
Tetrahedron
, vol.49
, pp. 7997-8006
-
-
Augy-Dorey, S.1
Dalko, P.2
Géro, S.D.3
Quiclet-Sire, B.4
Eustache, J.5
Stütz, P.6
-
15
-
-
0025704896
-
-
(e) Ogawa, S.; Nishi, K.; Shibata, Y. Carbohydr. Res. 1990, 206, 352-360.
-
(1990)
Carbohydr. Res.
, vol.206
, pp. 352-360
-
-
Ogawa, S.1
Nishi, K.2
Shibata, Y.3
-
16
-
-
37049076284
-
-
(f) Barton, D. H.; Géro, S. D.; Augy, S.; Quiclet-Sire, B. Chem. Commun. 1986, 18, 1399-1401.
-
(1986)
Chem. Commun.
, vol.18
, pp. 1399-1401
-
-
Barton, D.H.1
Géro, S.D.2
Augy, S.3
Quiclet-Sire, B.4
-
17
-
-
0033690703
-
-
Reviews: (a) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929-1972.
-
(2000)
Chem. Rev.
, vol.100
, pp. 1929-1972
-
-
Casiraghi, G.1
Zanardi, F.2
Appendino, G.3
Rassu, G.4
-
20
-
-
0037007735
-
-
(a) Barnes, D. M.; McLaughlin, M. A.; Oie, T.; Rasmussen, M. W.; Stewart, K. D.; Wittenberger, S. J. Org. Lett. 2092, 4, 1427-1430.
-
(2092)
Org. Lett.
, vol.4
, pp. 1427-1430
-
-
Barnes, D.M.1
McLaughlin, M.A.2
Oie, T.3
Rasmussen, M.W.4
Stewart, K.D.5
Wittenberger, S.J.6
-
21
-
-
0037047524
-
-
(b) DeGoey, D. A.; Chen, H.-J.; Flosi, W. J.; Grampovnik, D. J.; Yeung, C. M.; Klein, L. L.; Kempf, D. J. J. Org. Chem. 2002, 67, 5445-5453.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 5445-5453
-
-
DeGoey, D.A.1
Chen, H.-J.2
Flosi, W.J.3
Grampovnik, D.J.4
Yeung, C.M.5
Klein, L.L.6
Kempf, D.J.7
-
22
-
-
0033523222
-
-
(c) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990-6997.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 6990-6997
-
-
Martin, S.F.1
Barr, K.J.2
Smith, D.W.3
Bur, S.K.4
-
24
-
-
0034614462
-
-
(e) Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326. See also: Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733-772.
-
(2000)
Tetrahedron
, vol.56
, pp. 323-326
-
-
Lombardo, M.1
Trombini, C.2
-
25
-
-
0037363116
-
-
(e) Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326. See also: Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733-772.
-
(2003)
Chem. Rev.
, vol.103
, pp. 733-772
-
-
Dilman, A.D.1
Ioffe, S.L.2
-
26
-
-
1442267471
-
-
note
-
A screen of various silyl trifiates (TMSOTf, TESOTf, TBSOTf, TIPSOTf) indicated commercial TBSOTf to be the optimal promoter in this reaction.
-
-
-
-
27
-
-
1442292012
-
-
note
-
A plausible transition state to anti,anti-configured adduct 5 involves a synclinal-type approach of the silyloxy diene C(5) re-face to the C(1) si-face of the imine acceptor according to a relatively uncongested open-chain (Felkin-Ahn) model described here.
-
-
-
-
28
-
-
1442292010
-
-
note
-
In truth, the alternative cyclization protocol A to B was actually attempted. However, the extremely low yields obtained in elaborating adduct 6 into a suitably protected aldehyde lactone of type A (i.e., NPG = Cbz; OPG = TES) forced us to back down from this strategic option and follow the second and more fruitful route reported in this study.
-
-
-
-
29
-
-
0033538635
-
-
Rodríguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J. Tetrahedron Lett. 1999, 40, 5161-5164.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 5161-5164
-
-
Rodríguez, A.1
Nomen, M.2
Spur, B.W.3
Godfroid, J.J.4
-
30
-
-
0346780619
-
-
For a recent example of a silylative Mukaiyama intermolecular aldol reaction with TBSOTf and Hünig's base, see: Jung, M. E.; van den Heuvel, A. Org. Lett. 2003, 5, 4705-4707. See also: Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
-
(2003)
Org. Lett.
, vol.5
, pp. 4705-4707
-
-
Jung, M.E.1
Van Den Heuvel, A.2
-
31
-
-
0037160423
-
-
For a recent example of a silylative Mukaiyama intermolecular aldol reaction with TBSOTf and Hünig's base, see: Jung, M. E.; van den Heuvel, A. Org. Lett. 2003, 5, 4705-4707. See also: Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 392-393
-
-
Evans, D.A.1
Tedrow, J.S.2
Shaw, J.T.3
Downey, C.W.4
-
32
-
-
1442316466
-
-
note
-
Stereochemical proofs for 12, as well as 1 and 2·HCl, are compiled in the Supporting Information (Tables S1-S3).
-
-
-
-
33
-
-
0000055748
-
-
Hassner, A., Ed.; JAI Press: Stamford, CT
-
Representative reviews: (a) Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford, CT, 1998; Vol. 3, pp 113-189.
-
(1998)
Advances in Asymmetric Synthesis
, vol.3
, pp. 113-189
-
-
Casiraghi, G.1
Rassu, G.2
Zanardi, F.3
Battistini, L.4
-
34
-
-
0032875333
-
-
(b) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Synlett 1999, 1333-1350.
-
(1999)
Synlett
, pp. 1333-1350
-
-
Rassu, G.1
Zanardi, F.2
Battistini, L.3
Casiraghi, G.4
-
35
-
-
0034421824
-
-
(c) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Chem. Soc. Rev. 2000, 109-118.
-
(2000)
Chem. Soc. Rev.
, pp. 109-118
-
-
Rassu, G.1
Zanardi, F.2
Battistini, L.3
Casiraghi, G.4
-
37
-
-
1442341005
-
-
note
-
Interestingly, 1 and ent-1 can be viewed as new, locked hydroxyethylene isosteres of D-Ser-D-Ser and L-Ser-L-Ser dipeptides, respectively.
-
-
-
-
38
-
-
0001155380
-
-
Abell, A., Ed.; JAI Press: Stamford, CT
-
Lohof, E.; Burkhart, F.; Born, M. A.; Pflanker, E.; Kessler, H. In Advances in Amino Acid Mimetics and Peptidomimetics; Abell, A., Ed.; JAI Press: Stamford, CT, 1999; Vol. 2, pp 263-292.
-
(1999)
Advances in Amino Acid Mimetics and Peptidomimetics
, vol.2
, pp. 263-292
-
-
Lohof, E.1
Burkhart, F.2
Born, M.A.3
Pflanker, E.4
Kessler, H.5
|