-
1
-
-
0037301239
-
-
2.
-
2.
-
-
-
-
2
-
-
34250738671
-
-
Presented in part at the 229th American Chemical Society National Meeting, San Diego, CA, March 13-17, 2005, ORGN abstract 417.
-
Presented in part at the 229th American Chemical Society National Meeting, San Diego, CA, March 13-17, 2005, ORGN abstract 417.
-
-
-
-
3
-
-
33750944034
-
-
For the purported synthesis of the 12R,13R,18R diastereomer (numbering as in Scheme 1), see: S. Yu, F. Liu, D. Ma, Tetrahedron Lett. 2006, 47, 9155-9157. However, the NMR spectroscopic data are consistent with a Z isomer of the triene unit (see reference [20]).
-
For the purported synthesis of the 12R,13R,18R diastereomer (numbering as in Scheme 1), see: S. Yu, F. Liu, D. Ma, Tetrahedron Lett. 2006, 47, 9155-9157. However, the NMR spectroscopic data are consistent with a Z isomer of the triene unit (see reference [20]).
-
-
-
-
4
-
-
27144499809
-
-
For a nonstereoselective, biogenic synthesis from pseudotrienic acid A, see
-
For a nonstereoselective, biogenic synthesis from pseudotrienic acid A, see: A. Pohanka, A. Broberg, M. Johansson, L. Kenne, J. Levenfors, J. Nat. Prod. 2005, 68, 1380-1385.
-
(2005)
J. Nat. Prod
, vol.68
, pp. 1380-1385
-
-
Pohanka, A.1
Broberg, A.2
Johansson, M.3
Kenne, L.4
Levenfors, J.5
-
5
-
-
0037300511
-
-
K. Fujine, F. Abe, N. Seki, H. Ueda, M. Hino, T. Fujii, J. Antibiot. 2003, 56, 62-67.
-
(2003)
J. Antibiot
, vol.56
, pp. 62-67
-
-
Fujine, K.1
Abe, F.2
Seki, N.3
Ueda, H.4
Hino, M.5
Fujii, T.6
-
6
-
-
0037300435
-
-
K. Fujine, H. Ueda, M. Hino, T. Fujii, J. Antibiot. 2003, 56, 68-71.
-
(2003)
J. Antibiot
, vol.56
, pp. 68-71
-
-
Fujine, K.1
Ueda, H.2
Hino, M.3
Fujii, T.4
-
7
-
-
34250731058
-
-
There are four possible enantiomeric pairs that correspond to the structural formula of FR252921. Each pair is diastereomeric with respect to the other three pairs. Thus, when analyzed in conjunction with optical rotation or chiral-phase chromatography, one isomer from each of the diastereomeric pairs (that is, a total of four) contains the minimum stereoarray needed to establish the relative and absolute configuration of FR252921
-
There are four possible enantiomeric pairs that correspond to the structural formula of FR252921. Each pair is diastereomeric with respect to the other three pairs. Thus, when analyzed in conjunction with optical rotation or chiral-phase chromatography, one isomer from each of the diastereomeric pairs (that is, a total of four) contains the minimum stereoarray needed to establish the relative and absolute configuration of FR252921.
-
-
-
-
8
-
-
34250734252
-
-
Available NMR spectroscopic data were most consistent with an anti configuration of the methyl and hydroxy groups at C12 and C13.
-
Available NMR spectroscopic data were most consistent with an anti configuration of the methyl and hydroxy groups at C12 and C13.
-
-
-
-
9
-
-
34250693371
-
-
The 4-amino-(3R)-hydroxy-(2S)-methylbutanoyl subunit occurs in other bioactive natural products; see, for example: D. Amans, V. Bellosta, J. Cossy, Angew. Chem. 2006, 118, 6002-6004;
-
The 4-amino-(3R)-hydroxy-(2S)-methylbutanoyl subunit occurs in other bioactive natural products; see, for example: D. Amans, V. Bellosta, J. Cossy, Angew. Chem. 2006, 118, 6002-6004;
-
-
-
-
10
-
-
33748547631
-
-
Angew. Chem. Int. Ed. 2006, 45, 5870-5874.
-
(2006)
Chem. Int. Ed
, vol.45
, pp. 5870-5874
-
-
Angew1
-
11
-
-
0034670324
-
-
For an alternative synthesis of 2 and its Z,E isomer, see: B. B. Snider, T. Liu, J. Org. Chem. 2000, 65, 8490-8498.
-
For an alternative synthesis of 2 and its Z,E isomer, see: B. B. Snider, T. Liu, J. Org. Chem. 2000, 65, 8490-8498.
-
-
-
-
12
-
-
34250717687
-
-
2 methodology proved impractical logistically on a large scale. Wittig olefination with commercial 2-(triphenylphosphoranylidene) propionaldehyde furnished an 8:1 mixture of E and Z isomers in moderate yield.
-
2 methodology proved impractical logistically on a large scale. Wittig olefination with commercial 2-(triphenylphosphoranylidene) propionaldehyde furnished an 8:1 mixture of E and Z isomers in moderate yield.
-
-
-
-
13
-
-
0034708574
-
-
S.-i. Fukuzawa, H. Matsuzawa, S.-i. Yoshimitsu, J. Org. Chem. 2000, 65, 1702-1706.
-
(2000)
J. Org. Chem
, vol.65
, pp. 1702-1706
-
-
Fukuzawa, S.-I.1
Matsuzawa, H.2
Yoshimitsu, S.-I.3
-
14
-
-
33746048429
-
-
Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 9066-9073
-
-
Zhang, Z.1
Liu, C.2
Kinder, R.E.3
Han, X.4
Qian, H.5
Widenhoefer, R.A.6
-
15
-
-
33644955826
-
-
B. Liang, T. Novak, Z. Tan, E. Negishi, J. Am. Chem. Soc. 2006, 128, 2770-2771.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 2770-2771
-
-
Liang, B.1
Novak, T.2
Tan, Z.3
Negishi, E.4
-
16
-
-
0032747809
-
-
J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 9550-9561
-
-
Wolfe, J.P.1
Singer, R.A.2
Yang, B.H.3
Buchwald, S.L.4
-
17
-
-
0012016624
-
-
D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129.
-
(1981)
J. Am. Chem. Soc
, vol.103
, pp. 2127-2129
-
-
Evans, D.A.1
Bartroli, J.2
Shih, T.L.3
-
18
-
-
33748512153
-
-
M. J. Schnermann, F. A. Romero, I. Hwang, E. Nakamaru-Ogiso, T. Yagi, D. L. Boger, J. Am. Chem. Soc. 2006, 128, 11 799-11 807.
-
(2006)
J. Am. Chem. Soc
, vol.128
-
-
Schnermann, M.J.1
Romero, F.A.2
Hwang, I.3
Nakamaru-Ogiso, E.4
Yagi, T.5
Boger, D.L.6
-
19
-
-
33645452024
-
-
M. Reggelin, B. Junker, T. Heinrich, S. Slavik, P. Buehle, J. Am. Chem. Soc. 2006, 128, 4023-4034.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 4023-4034
-
-
Reggelin, M.1
Junker, B.2
Heinrich, T.3
Slavik, S.4
Buehle, P.5
-
20
-
-
0029656223
-
-
K. Iseki, S. Oishi, Y. Kobayashi, Tetrahedron 1996, 52, 71-84.
-
(1996)
Tetrahedron
, vol.52
, pp. 71-84
-
-
Iseki, K.1
Oishi, S.2
Kobayashi, Y.3
-
21
-
-
34250753089
-
-
4NF/HOAc, pyridinium p-toluenesulfonate) after lactonization engendered a host of complications, including intra/intermolecular Michael addition, β elimination, trans lactonization, and, most notably, a facile E/Z isomerization of the triene.
-
4NF/HOAc, pyridinium p-toluenesulfonate) after lactonization engendered a host of complications, including intra/intermolecular Michael addition, β elimination, trans lactonization, and, most notably, a facile E/Z isomerization of the triene.
-
-
-
-
22
-
-
0025106114
-
-
A. B. Jones, A. Villalobos, R. G. Linde, S. J. Danishefsky, J. Org. Chem. 1990, 55, 2786-2797.
-
(1990)
J. Org. Chem
, vol.55
, pp. 2786-2797
-
-
Jones, A.B.1
Villalobos, A.2
Linde, R.G.3
Danishefsky, S.J.4
-
23
-
-
33645364955
-
-
For a review on macrolactonization, see
-
For a review on macrolactonization, see: A. Parenty, X. Moreau, J.-M. Campagne, Chem. Rev. 2006, 106, 911-939.
-
(2006)
Chem. Rev
, vol.106
, pp. 911-939
-
-
Parenty, A.1
Moreau, X.2
Campagne, J.-M.3
-
24
-
-
85077634689
-
-
Among the many procedures attempted, those described in the following articles also proved unsatisfactory: a O. Mitsunobu, Synthesis 1981, 1-28;
-
Among the many procedures attempted, those described in the following articles also proved unsatisfactory: a) O. Mitsunobu, Synthesis 1981, 1-28;
-
-
-
-
26
-
-
23844499421
-
-
c) Y. Oohashi, K. Fukumoto, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2005, 78, 1508-1519;
-
(2005)
Bull. Chem. Soc. Jpn
, vol.78
, pp. 1508-1519
-
-
Oohashi, Y.1
Fukumoto, K.2
Mukaiyama, T.3
-
27
-
-
0001616071
-
-
d) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
-
(1979)
Bull. Chem. Soc. Jpn
, vol.52
, pp. 1989-1993
-
-
Inanaga, J.1
Hirata, K.2
Saeki, H.3
Katsuki, T.4
Yamaguchi, M.5
-
28
-
-
0037078348
-
-
I. Shiina, M. Kubota, R. Ibuka, Tetrahedron Lett. 2002, 43, 7535-7539.
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 7535-7539
-
-
Shiina, I.1
Kubota, M.2
Ibuka, R.3
|