-
1
-
-
37049138737
-
-
S. M. Kupchan, R. L. Baxter, C.-K. Chiang, C. J. Gilmore, R. F. Bryan, J. Chem. Soc. Chem. Commun. 1973, 842-843.
-
(1973)
J. Chem. Soc. Chem. Commun.
, pp. 842-843
-
-
Kupchan, S.M.1
Baxter, R.L.2
Chiang, C.-K.3
Gilmore, C.J.4
Bryan, R.F.5
-
2
-
-
0019129930
-
-
P. A. Grieco, T. Oguri, S. Oilman, J. Am. Chem. Soc. 1980, 102, 5886-5891.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 5886-5891
-
-
Grieco, P.A.1
Oguri, T.2
Oilman, S.3
-
4
-
-
0023712883
-
-
b) T. Wakamatsu, N. Miyachi, F. Ozaki, M. Shibasaki, Y. Ban, Tetrahedron Lett. 1988, 29, 3829-3832.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 3829-3832
-
-
Wakamatsu, T.1
Miyachi, N.2
Ozaki, F.3
Shibasaki, M.4
Ban, Y.5
-
5
-
-
2742605030
-
-
Review on sultone chemistry: P. Metz, J. Prakt. Chem. 1998, 340, 1-10.
-
(1998)
J. Prakt. Chem.
, vol.340
, pp. 1-10
-
-
Metz, P.1
-
6
-
-
0000356506
-
-
Isolation: a) B.-N. Zhou, N.-S. Bai, L.-Z. Ling, G. A. Cordell, Phytochemistry 1993, 34, 249-252;
-
(1993)
Phytochemistry
, vol.34
, pp. 249-252
-
-
Zhou, B.-N.1
Bai, N.-S.2
Ling, L.-Z.3
Cordell, G.A.4
-
7
-
-
0027135651
-
-
b) F. Jeske, S. Huneck, J. Jakupovic, Phytochemistry 1993, 34, 1647-1649.
-
(1993)
Phytochemistry
, vol.34
, pp. 1647-1649
-
-
Jeske, F.1
Huneck, S.2
Jakupovic, J.3
-
8
-
-
9244230301
-
-
US 6,627,623 B2, 2003
-
Compounds 3 and 4 effect phosphorylation of the antiapoptosis protein Bcl-2 and induce apoptosis in several cancer cell lines; for 4 cell-cycle arrest at the G2/M phase as well as polymerization of microtubules was proven: C.-T. Ho, M. Rafi, R. S. Dipaola, G. Ghai, R. T. Rosen, N. Bai, US 6,627,623 B2, 2003.
-
-
-
Ho, C.-T.1
Rafi, M.2
Dipaola, R.S.3
Ghai, G.4
Rosen, R.T.5
Bai, N.6
-
9
-
-
0037359287
-
-
For the relative configuration of 3 and 4 shown in Scheme 1, see ref. [5b] as well as the crystal structures of 3 depicted in: a) A.-R. Han, W. Mar, E.-K. Seo, Nat. Prod. Sci. 2003, 9, 28-30;
-
(2003)
Nat. Prod. Sci.
, vol.9
, pp. 28-30
-
-
Han, A.-R.1
Mar, W.2
Seo, E.-K.3
-
10
-
-
1242339561
-
-
b) S. Liu, H. Liu, W. Yan, L. Zhang, N. Bai, C.-T. Ho, Bioorg. Med. Chem. Lett. 2004, 14, 1101-1104.
-
(2004)
Bioorg. Med. Chem. Lett.
, vol.14
, pp. 1101-1104
-
-
Liu, S.1
Liu, H.2
Yan, W.3
Zhang, L.4
Bai, N.5
Ho, C.-T.6
-
11
-
-
0001081053
-
-
P. Metz, J. Stölting, M. Läge, B. Krebs, Angew. Chem. 1994, 106, 2275-2276; Angew. Chem. Int. Ed. Engl. 1994, 33, 2195-2197.
-
(1994)
Angew. Chem.
, vol.106
, pp. 2275-2276
-
-
Metz, P.1
Stölting, J.2
Läge, M.3
Krebs, B.4
-
12
-
-
33748657657
-
-
P. Metz, J. Stölting, M. Läge, B. Krebs, Angew. Chem. 1994, 106, 2275-2276; Angew. Chem. Int. Ed. Engl. 1994, 33, 2195-2197.
-
(1994)
Angew. Chem. Int. Ed. Engl.
, vol.33
, pp. 2195-2197
-
-
-
13
-
-
0037148428
-
-
A. Bierstedt, J. Stölting, R. Fröhlich, P. Metz, Tetrahedron: Asymmetry 2001, 12, 3399-3407.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 3399-3407
-
-
Bierstedt, A.1
Stölting, J.2
Fröhlich, R.3
Metz, P.4
-
14
-
-
0041736497
-
-
T. Hamada, T. Torii, K. Izawa, R. Noyori, T. Ikariya, Org. Lett. 2002, 4, 4373-4376.
-
(2002)
Org. Lett.
, vol.4
, pp. 4373-4376
-
-
Hamada, T.1
Torii, T.2
Izawa, K.3
Noyori, R.4
Ikariya, T.5
-
15
-
-
0025857682
-
-
J. Dubac, A. Gaset, M. Maraval, Synth. Commun. 1991, 21, 11-16.
-
(1991)
Synth. Commun.
, vol.21
, pp. 11-16
-
-
Dubac, J.1
Gaset, A.2
Maraval, M.3
-
16
-
-
0000374349
-
-
This unusual regioselectivity of epoxide opening was already reported for racemic 8: B. Alcaide, P. Areces, E. Borredon, C. Biurrun, J. P. Castells, J. Plumet, Heterocycles 1990, 31, 1997-2002. We found that the stereochemical course is strongly dependent on the nature of the methyl nucleophile. With methylmagnesium bromide, again regioisomer 9 is preferentially formed; however, the reaction proceeds with extensive racemization.
-
(1990)
Heterocycles
, vol.31
, pp. 1997-2002
-
-
Alcaide, B.1
Areces, P.2
Borredon, E.3
Biurrun, C.4
Castells, J.P.5
Plumet, J.6
-
20
-
-
0034791734
-
-
B. Plietker, D. Seng, R. Fröhlich, P. Metz, Eur. J. Org. Chem. 2001, 3669-3676.
-
(2001)
Eur. J. Org. Chem.
, pp. 3669-3676
-
-
Plietker, B.1
Seng, D.2
Fröhlich, R.3
Metz, P.4
-
23
-
-
0001712831
-
-
S. Arumugam, D. McLeod, J. G. Verkade, J. Org. Chem. 1998, 63, 3677-3679.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3677-3679
-
-
Arumugam, S.1
McLeod, D.2
Verkade, J.G.3
-
27
-
-
9244226236
-
-
note
-
Apparently the intermediate allylcarbenium ion is trapped by the solvent DMF as the nucleophile to generate an immonium ion, which is converted to the formate during aqueous workup.
-
-
-
-
30
-
-
0002445083
-
-
B. Deguin, J.-C. Florent, C. Monneret, J. Org. Chem. 1991, 56, 405-411.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 405-411
-
-
Deguin, B.1
Florent, J.-C.2
Monneret, C.3
-
31
-
-
9244223865
-
-
note
-
Experiments toward Mitsunobu inversion at C6 in 24 were not successful.
-
-
-
-
32
-
-
9244255025
-
-
note
-
Increasing the reaction temperature in order to achieve complete reduction caused desilylation of the secondary silyl ether.
-
-
-
-
34
-
-
0030803863
-
-
a) J. S. Debenham, R. Rodebaugh, B. Fraser-Reid, J. Org. Chem. 1997, 62, 4591-4600;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4591-4600
-
-
Debenham, J.S.1
Rodebaugh, R.2
Fraser-Reid, B.3
-
35
-
-
0030805117
-
-
b) D. L. Boger, R. M. Borzilleri, S. Nukui, R. T. Beresis, J. Org. Chem. 1997, 62, 4721-4736.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4721-4736
-
-
Boger, D.L.1
Borzilleri, R.M.2
Nukui, S.3
Beresis, R.T.4
-
36
-
-
0000458209
-
-
A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
-
(1993)
Chem. Rev.
, vol.93
, pp. 1307-1370
-
-
Hoveyda, A.H.1
Evans, D.A.2
Fu, G.C.3
-
37
-
-
9244231521
-
-
note
-
In addition to 27 the C6-epimeric alcohol was isolated in 6% yield.
-
-
-
-
40
-
-
9244255024
-
-
note
-
b) Addition of molecular sieves 4 Å in the first step caused a significant increase in yield.
-
-
-
-
41
-
-
0037213016
-
-
T. M. Hansen, G. J. Florence, P. Lugo-Mas, J. Chen, J. N. Abrams, C. J. Forsyth, Tetrahedron Lett. 2003, 44, 57-59.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 57-59
-
-
Hansen, T.M.1
Florence, G.J.2
Lugo-Mas, P.3
Chen, J.4
Abrams, J.N.5
Forsyth, C.J.6
-
42
-
-
0034703414
-
-
B. Noya, M. D. Paredes, L. Ozores, R. Alonso, J. Org. Chem. 2000, 65, 5960-5968.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 5960-5968
-
-
Noya, B.1
Paredes, M.D.2
Ozores, L.3
Alonso, R.4
-
43
-
-
9244245499
-
-
note
-
3).
-
-
-
-
44
-
-
9244238960
-
-
-3, Flack parameter 0.04(19). Programs used: EXPRESS, MolEN, SHELXS-97, SHELXL-97, SCHAKAL. CCDC-239240 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
-
-
-
-
45
-
-
0025770669
-
-
B. Hartmann, A.M. Kanazawa, J. P. Deprés, A. E. Greene, Tetrahedron Lett. 1991, 32, 5077-5080.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 5077-5080
-
-
Hartmann, B.1
Kanazawa, A.M.2
Deprés, J.P.3
Greene, A.E.4
-
46
-
-
9244237292
-
-
note
-
3).
-
-
-
|