-
1
-
-
0021981588
-
-
Yasumoto, T.; Murata, M.; Oshima, Y.; Sano, M.; Matsumoto, G. K.; Clardy, J. Tetrahedron 1985, 41, 1019-1025.
-
(1985)
Tetrahedron
, vol.41
, pp. 1019-1025
-
-
Yasumoto, T.1
Murata, M.2
Oshima, Y.3
Sano, M.4
Matsumoto, G.K.5
Clardy, J.6
-
2
-
-
0032540486
-
-
(a) Sasaki, K.; Wright, J. L. C.; Yasumoto, T. J. Org. Chem. 1998, 63, 2475-2480.
-
(1998)
J. Org. Chem
, vol.63
, pp. 2475-2480
-
-
Sasaki, K.1
Wright, J.L.C.2
Yasumoto, T.3
-
3
-
-
0032392360
-
-
(b) Daiguji, M.; Satake, M.; James, K. J.; Bishop, A.; Mackenzie, L.; Naoki, H.; Yasumoto, T. Chem. Lett. 1998, 7, 653-654.
-
(1998)
Chem. Lett
, vol.7
, pp. 653-654
-
-
Daiguji, M.1
Satake, M.2
James, K.J.3
Bishop, A.4
Mackenzie, L.5
Naoki, H.6
Yasumoto, T.7
-
4
-
-
33746872853
-
-
(c) Wilkins, A. L.; Rehmann, N.; Torgersen, T. R.; Keogh, M.; Petersen, D.; Hess, P.; Rise, F.; Miles, C. O. J. Agric. Food. Chem. 2006, 54, 5672-5678.
-
(2006)
J. Agric. Food. Chem
, vol.54
, pp. 5672-5678
-
-
Wilkins, A.L.1
Rehmann, N.2
Torgersen, T.R.3
Keogh, M.4
Petersen, D.5
Hess, P.6
Rise, F.7
Miles, C.O.8
-
5
-
-
33746179987
-
-
and refs therein
-
(d) Miles, C. O.; Wilkins, A. L.; Hawkes, A. D.; Jensen, D. J.; Selwood, A. L; Beuzenberg, V.; MacKenzie, A. L.; Cooney, J. M.; Holland, P. T. Toxicon 2006, 48, 152-159, and refs therein.
-
(2006)
Toxicon
, vol.48
, pp. 152-159
-
-
Miles, C.O.1
Wilkins, A.L.2
Hawkes, A.D.3
Jensen, D.J.4
Selwood, A.L.5
Beuzenberg, V.6
MacKenzie, A.L.7
Cooney, J.M.8
Holland, P.T.9
-
6
-
-
61349189829
-
-
For selected examples, see: (a) Japan: see ref 1, 2a,b
-
For selected examples, see: (a) Japan: see ref 1, 2a,b.
-
-
-
-
7
-
-
0029603564
-
-
Korea: Jung, J. H.; Sim, C. J.; Lee, C.-O. J. Nat. Prod. 1995, 58, 1722-1726.
-
(b) Korea: Jung, J. H.; Sim, C. J.; Lee, C.-O. J. Nat. Prod. 1995, 58, 1722-1726.
-
-
-
-
8
-
-
33749557613
-
-
New Zealand and Norway: see ref 2d, d) Ireland: see ref 2c, e Finland: Kuuppo, P, Uronen, P, Petermann, A, Tamminen, T, Granéli, E. Limnol. Oceanogr. 2006, 51, 2300-2307
-
(c) New Zealand and Norway: see ref 2d. (d) Ireland: see ref 2c. (e) Finland: Kuuppo, P.; Uronen, P.; Petermann, A.; Tamminen, T.; Granéli, E. Limnol. Oceanogr. 2006, 51, 2300-2307.
-
-
-
-
9
-
-
0032829103
-
-
(a) Spector, I.; Braet, F.; Schochet, N. R.; Bubb, M. R. Microscop. Res. Technol. 1999,47, 18-37.
-
(1999)
Microscop. Res. Technol
, vol.47
, pp. 18-37
-
-
Spector, I.1
Braet, F.2
Schochet, N.R.3
Bubb, M.R.4
-
10
-
-
0036609451
-
-
(b) Leira, F.; Cabadon, A. G.; Vieytes, M. R.; Roman, Y.; Alfonso, A.; Botana, L. M.; Yasumoto, T.; Malaguti, C.; Rossini, G. P. Biochem. Pharmacol. 2002, 63, 1979-1988.
-
(2002)
Biochem. Pharmacol
, vol.63
, pp. 1979-1988
-
-
Leira, F.1
Cabadon, A.G.2
Vieytes, M.R.3
Roman, Y.4
Alfonso, A.5
Botana, L.M.6
Yasumoto, T.7
Malaguti, C.8
Rossini, G.P.9
-
11
-
-
85047698843
-
-
For total synthesis of PTX4 and PTX8, see: (a) Evans, D. A.; Rajapakse, H. A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4569-4573.
-
For total synthesis of PTX4 and PTX8, see: (a) Evans, D. A.; Rajapakse, H. A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4569-4573.
-
-
-
-
12
-
-
85047698843
-
-
For other synthetic approaches, see
-
(b) Evans, D. A.; Rajapakse, H. A.; Chiu, A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4573-4576. For other synthetic approaches, see:
-
(2002)
Angew. Chem., Int. Ed
, vol.41
, pp. 4573-4576
-
-
Evans, D.A.1
Rajapakse, H.A.2
Chiu, A.3
Stenkamp, D.4
-
16
-
-
0037149678
-
-
(f) Paquette, L. A.; Peng, X.; Bondar, D. Org. Lett. 2002, 4, 937-940.
-
(2002)
Org. Lett
, vol.4
, pp. 937-940
-
-
Paquette, L.A.1
Peng, X.2
Bondar, D.3
-
17
-
-
4544329386
-
-
(g) Peng, X.; Bondar, D.; Paquette, L. A. Tetrahedron 2004, 60, 9589-9598.
-
(2004)
Tetrahedron
, vol.60
, pp. 9589-9598
-
-
Peng, X.1
Bondar, D.2
Paquette, L.A.3
-
18
-
-
18844417940
-
-
(h) Bondar, D.; Liu, J.; Müller, T.; Paquette, L. A. Org. Lett. 2005, 7, 1813-1816.
-
(2005)
Org. Lett
, vol.7
, pp. 1813-1816
-
-
Bondar, D.1
Liu, J.2
Müller, T.3
Paquette, L.A.4
-
19
-
-
29844434137
-
-
(i) Halim, R.; Brimble, M. A.; Merten, J. Org. Lett. 2005, 7, 2659-2662.
-
(2005)
Org. Lett
, vol.7
, pp. 2659-2662
-
-
Halim, R.1
Brimble, M.A.2
Merten, J.3
-
20
-
-
20544471398
-
-
(j) Fujiwara, K.; Kobayashi, M.; Yamamoto, F.; Aki, Y.; Kawamura, M.; Awakura, D.; Amano, S.; Okano, A.; Murai, A.; Hawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 5067-5069.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 5067-5069
-
-
Fujiwara, K.1
Kobayashi, M.2
Yamamoto, F.3
Aki, Y.4
Kawamura, M.5
Awakura, D.6
Amano, S.7
Okano, A.8
Murai, A.9
Hawai, H.10
Suzuki, T.11
-
21
-
-
33645305180
-
-
(k) Halim, R.; Brimble, M. A.; Merten, J. Org. Biomol. Chem. 2006, 4, 1387-1399.
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 1387-1399
-
-
Halim, R.1
Brimble, M.A.2
Merten, J.3
-
22
-
-
34249288615
-
-
(l) Fujiwara, K.; Aki, Y.; Yamamoto, F.; Kawamura, M.; Kobayashi, M.; Okano, A.; Awakura, D.; Shiga, S.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2007, 48, 4523-4527.
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 4523-4527
-
-
Fujiwara, K.1
Aki, Y.2
Yamamoto, F.3
Kawamura, M.4
Kobayashi, M.5
Okano, A.6
Awakura, D.7
Shiga, S.8
Murai, A.9
Kawai, H.10
Suzuki, T.11
-
24
-
-
33847638000
-
-
(n) O'Connor, P. D.; Knight, C. K.; Friedrich, D.; Peng, X.; Paquette, L. A. J. Org. Chem. 2007, 72, 1747-1754.
-
(2007)
J. Org. Chem
, vol.72
, pp. 1747-1754
-
-
O'Connor, P.D.1
Knight, C.K.2
Friedrich, D.3
Peng, X.4
Paquette, L.A.5
-
26
-
-
33947180954
-
-
(p) Lotesta, S. D.; Hou, Y.; Williams, L. J. Org. Lett. 2007, 9, 869-872.
-
(2007)
Org. Lett
, vol.9
, pp. 869-872
-
-
Lotesta, S.D.1
Hou, Y.2
Williams, L.J.3
-
28
-
-
0003000271
-
-
For additions of organometallic reagents to ́-hydroxyketones, see: a
-
For additions of organometallic reagents to ́-hydroxyketones, see: (a) Ukaji, Y.; Kanda, H.; Yamamoto, K.; Fujisawa, T. Chem. Lett. 1990, 597-600.
-
(1990)
Chem. Lett
, pp. 597-600
-
-
Ukaji, Y.1
Kanda, H.2
Yamamoto, K.3
Fujisawa, T.4
-
29
-
-
0030065710
-
-
(b) Ruano, J. L. G.; Tito, A.; Culebras, R. Tetrahedron 1996, 52, 2177-2186.
-
(1996)
Tetrahedron
, vol.52
, pp. 2177-2186
-
-
Ruano, J.L.G.1
Tito, A.2
Culebras, R.3
-
30
-
-
0001428047
-
-
(a) Corey, E. J.; Kim, C. U.; Chen, R. H. K.; Takeda, M. J. Am. Chem. Soc. 1972, 94, 4395-4396.
-
(1972)
J. Am. Chem. Soc
, vol.94
, pp. 4395-4396
-
-
Corey, E.J.1
Kim, C.U.2
Chen, R.H.K.3
Takeda, M.4
-
31
-
-
0001077697
-
-
(b) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Am. Chem. Soc. 1990, 112, 4404-4410.
-
(1990)
J. Am. Chem. Soc
, vol.112
, pp. 4404-4410
-
-
Lipshutz, B.H.1
Ellsworth, E.L.2
Dimock, S.H.3
Smith, R.A.J.4
-
32
-
-
61349119493
-
-
The entire synthetic sequence was successfully scaled up to ca. a 20 g scale
-
The entire synthetic sequence was successfully scaled up to ca. a 20 g scale.
-
-
-
-
33
-
-
55449096098
-
-
The stereochemistry of the aldol and the methyltitanation steps was established by extensive NOE studies of the CDE and CDEF ring systems. See the following paper in this issue: Helmboldt, H.; Aho, J. E.; Pihko, P. M. Org. Lett. 2008, 10, 4183-4185.
-
The stereochemistry of the aldol and the methyltitanation steps was established by extensive NOE studies of the CDE and CDEF ring systems. See the following paper in this issue: Helmboldt, H.; Aho, J. E.; Pihko, P. M. Org. Lett. 2008, 10, 4183-4185.
-
-
-
-
34
-
-
10244265483
-
-
For excellent discussions and predictions in both cyclic and acyclic systems, see
-
(a) Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 11, 2-127. For excellent discussions and predictions in both cyclic and acyclic systems, see:
-
(1959)
J. Chem. Soc
, vol.11
, pp. 2-127
-
-
Cornforth, J.W.1
Cornforth, R.H.2
Mathew, K.K.3
-
35
-
-
33746333004
-
-
Evans, D. A.; Cee, V. J.; Siska, S. J. J. Am. Chem. Soc. 2006, 128, 9433-9441, and refs therein. The high level of diastereoselection observed suggests that the α,β relationship of the oxygen substituents in 3 represents a stereochemically reinforcing case. For a related highly selective aldol bond construction, see:
-
(b) Evans, D. A.; Cee, V. J.; Siska, S. J. J. Am. Chem. Soc. 2006, 128, 9433-9441, and refs therein. The high level of diastereoselection observed suggests that the α,β relationship of the oxygen substituents in 3 represents a stereochemically reinforcing case. For a related highly selective aldol bond construction, see:
-
-
-
-
36
-
-
0035681095
-
-
(c) Anderson, O. P.; Barren, A. G. M.; Edmunds, J. J.; Hachiya, S.-I.; Hendrix, J. A.; Horita, K.; Malecha, J. W.; Parkinson, C. J.; VanSickle, A. Can. J. Chem. 2001, 79, 1562-1592.
-
(2001)
Can. J. Chem
, vol.79
, pp. 1562-1592
-
-
Anderson, O.P.1
Barren, A.G.M.2
Edmunds, J.J.3
Hachiya, S.-I.4
Hendrix, J.A.5
Horita, K.6
Malecha, J.W.7
Parkinson, C.J.8
VanSickle, A.9
-
37
-
-
49949128203
-
-
(a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199-2204.
-
(1968)
Tetrahedron Lett
, vol.9
, pp. 2199-2204
-
-
Chérest, M.1
Felkin, H.2
Prudent, N.3
-
41
-
-
61349140765
-
-
See Supporting Information for further details
-
See Supporting Information for further details.
-
-
-
-
42
-
-
33845278140
-
-
There are two possible modes to achieve 1,3-induction in hydroxyl-directed additions: the nucleophile is delivered either externally (from an external reagent) or internally (directed addition): (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. A chelation-controlled transition state model has also been suggested,
-
There are two possible modes to achieve 1,3-induction in hydroxyl-directed additions: the nucleophile is delivered either externally (from an external reagent) or internally (directed addition): (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. A chelation-controlled transition state model has also been suggested,
-
-
-
-
43
-
-
0001394520
-
-
Chem. Soc, For a review, see
-
(b) Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833-4835. For a review, see:
-
(1983)
J. Am
, vol.105
, pp. 4833-4835
-
-
Reetz, M.T.1
Jung, A.2
-
45
-
-
61349129580
-
-
For further details, including screens for different solvents and additives, see Supporting Information
-
For further details, including screens for different solvents and additives, see Supporting Information.
-
-
-
-
46
-
-
0000044737
-
-
Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421-1440.
-
(1985)
Chem. Ber
, vol.118
, pp. 1421-1440
-
-
Reetz, M.T.1
Westermann, J.2
Steinbach, R.3
Wenderoth, B.4
Peter, R.5
Ostarek, R.6
Maus, S.7
-
47
-
-
1142291707
-
-
Excess Ti(OiPr)4 should facilitate the removal of the product from the metal center and assist in the formation of an active complex
-
4 should facilitate the removal of the product from the metal center and assist in the formation of an active complex: Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588.
-
(2004)
Organometallics
, vol.23
, pp. 580-588
-
-
Wu, K.-H.1
Gau, H.-M.2
|