-
1
-
-
0000071433
-
-
Two-dimensional structure: a) H. H. Strain, W. A. Svec, K. Aitzetmüller, M. C. Grandolfo, J. J. Katz, H. Kjøsen, S. Norgård, S. Liaaen-Jensen, F. T. Haxo, P. Wegfahrt, H. Rapoport, J. Am. Chem. Soc. 1971, 93, 1823-1825;
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J. Am. Chem. Soc.
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, pp. 1823-1825
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-
Strain, H.H.1
Svec, W.A.2
Aitzetmüller, K.3
Grandolfo, M.C.4
Katz, J.J.5
Kjøsen, H.6
Norgård, S.7
Liaaen-Jensen, S.8
Haxo, F.T.9
Wegfahrt, P.10
Rapoport, H.11
-
2
-
-
0000910975
-
-
three-dimensional structure: b) J. E. Johansen, G. Borch, S. Liaaen-Jensen, Phytochemistry 1980, 19, 441-444;
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(1980)
Phytochemistry
, vol.19
, pp. 441-444
-
-
Johansen, J.E.1
Borch, G.2
Liaaen-Jensen, S.3
-
3
-
-
0000159736
-
-
c) H. H. Strain, W. A. Svec, P. Wegfahrt, H. Rapoport, F. T. Haxo, S. Norgård, H. Kjøsen, S. Liaaen-Jensen, Acta Chem. Scand. B 1976, 30, 109-120.
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(1976)
Acta Chem. Scand. B
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, pp. 109-120
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-
Strain, H.H.1
Svec, W.A.2
Wegfahrt, P.3
Rapoport, H.4
Haxo, F.T.5
Norgård, S.6
Kjøsen, H.7
Liaaen-Jensen, S.8
-
4
-
-
0026731296
-
-
J. A. Haugan, T. Aakermann, S. Liaaen-Jensen, Methods Enzymol. 1992, 213, 231-245.
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(1992)
Methods Enzymol.
, vol.213
, pp. 231-245
-
-
Haugan, J.A.1
Aakermann, T.2
Liaaen-Jensen, S.3
-
5
-
-
84971101883
-
-
For example, a) freelingyne (revised structure): C. F. Ingham, R. A. Massy-Westropp, Aust. J. Chem. 1974, 27, 1491-1503; p. 643 in D. W. Knight, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1975, 641-644;
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(1974)
Aust. J. Chem.
, vol.27
, pp. 1491-1503
-
-
Ingham, C.F.1
Massy-Westropp, R.A.2
-
6
-
-
37049140873
-
-
For example, a) freelingyne (revised structure): C. F. Ingham, R. A. Massy-Westropp, Aust. J. Chem. 1974, 27, 1491-1503; p. 643 in D. W. Knight, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1975, 641-644;
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(1975)
J. Chem. Soc. Perkin Trans. 1
, pp. 641-644
-
-
Knight, D.W.1
Pattenden, G.2
-
8
-
-
0001507883
-
-
c) pyrrhoxanthin, two-dimensional structure: J. E. Johansen, W. A. Svec, S. Liaaen-Jensen, F. T. Haxo, Phytochemistry 1974, 13, 2261-2271; three-dimensional structur: T. Aakermann, S. Liaaen-Jensen, Phytochemistry 1992, 31, 1779-1782;
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(1974)
Phytochemistry
, vol.13
, pp. 2261-2271
-
-
Johansen, J.E.1
Svec, W.A.2
Liaaen-Jensen, S.3
Haxo, F.T.4
-
9
-
-
0001413066
-
-
c) pyrrhoxanthin, two-dimensional structure: J. E. Johansen, W. A. Svec, S. Liaaen-Jensen, F. T. Haxo, Phytochemistry 1974, 13, 2261-2271; three-dimensional structur: T. Aakermann, S. Liaaen-Jensen, Phytochemistry 1992, 31, 1779-1782;
-
(1992)
Phytochemistry
, vol.31
, pp. 1779-1782
-
-
Aakermann, T.1
Liaaen-Jensen, S.2
-
10
-
-
0025027671
-
-
d) Cf. also xerulinic acid, xerulin, and dihydroxerulin, which, however, have no α substituent: D. Kuhnt, T. Anke, H. Besl, M. Bross, R. Herrmann, U. Mocek, B. Steffan, W. Steglich, J. Antibiot. 1990, 43, 1413-1420.
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(1990)
J. Antibiot.
, vol.43
, pp. 1413-1420
-
-
Kuhnt, D.1
Anke, T.2
Besl, H.3
Bross, M.4
Herrmann, R.5
Mocek, U.6
Steffan, B.7
Steglich, W.8
-
11
-
-
0030055628
-
-
E. Hofmann, P. M. Wrench, F. P. Sharples, R. G. Hiller, W. Welte, K. Diederichs, Science 1996, 272, 1788-1791.
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(1996)
Science
, vol.272
, pp. 1788-1791
-
-
Hofmann, E.1
Wrench, P.M.2
Sharples, F.P.3
Hiller, R.G.4
Welte, W.5
Diederichs, K.6
-
13
-
-
16244365117
-
-
ref. [3c]
-
γ-Alkylidenebutenolides are also part of the following carotenoids: a) peridinol: ref. [3c];
-
-
-
-
15
-
-
16244418344
-
-
ref. [3c]
-
c) pyrrhoxanthin: ref. [3c];
-
-
-
-
16
-
-
16244390808
-
-
ref. [3c]
-
d) pyrrhoxanthinol: ref. [3c];
-
-
-
-
17
-
-
0024084043
-
-
e) hydratopyrrhoxanthinol: S. Hertzberg, V. Partali, S. Liaaen-Jensen, Acta Chem. Scand. B 1988, 42, 495-503;
-
(1988)
Acta Chem. Scand. B
, vol.42
, pp. 495-503
-
-
Hertzberg, S.1
Partali, V.2
Liaaen-Jensen, S.3
-
18
-
-
46549095131
-
-
f) uriolide: P. Foss, R. R. L. Guillard, S. Liaaen-Jensen, Phytochemistry 1986, 25, 119-124;
-
(1986)
Phytochemistry
, vol.25
, pp. 119-124
-
-
Foss, P.1
Guillard, R.R.L.2
Liaaen-Jensen, S.3
-
20
-
-
16244423265
-
-
ref. [6g]
-
h) anhydrouriolide: ref. [6g];
-
-
-
-
21
-
-
16244386460
-
-
ref. [6g]
-
i) 3′-dehydrouriolide: ref. [6g];
-
-
-
-
22
-
-
0035007506
-
-
j) unnamed carotenoid: T. Maoka, K. Hashimoto, N. Akimoto, Y. Fuhiwara, J. Nat. Prod. 2001, 64, 578-581;
-
(2001)
J. Nat. Prod.
, vol.64
, pp. 578-581
-
-
Maoka, T.1
Hashimoto, K.2
Akimoto, N.3
Fuhiwara, Y.4
-
23
-
-
8644222906
-
-
k) unnamed carotenoid: M. Suzuki, K. Watanabe, S. Fujiwara, T. Kurasawa, T. Wakabayashi, M. Tsuzuki, K. Iguchi, T. Yamori, Chem. Pharm. Bull. 2003, 724-727.
-
(2003)
Chem. Pharm. Bull.
, pp. 724-727
-
-
Suzuki, M.1
Watanabe, K.2
Fujiwara, S.3
Kurasawa, T.4
Wakabayashi, T.5
Tsuzuki, M.6
Iguchi, K.7
Yamori, T.8
-
26
-
-
0030962724
-
-
Other approaches to γ-alkylidenebutenolides: a) E.-I. Negishi, M. Kotora, Tetrahedron 1997, 53, 6707-6738;
-
(1997)
Tetrahedron
, vol.53
, pp. 6707-6738
-
-
Negishi, E.-I.1
Kotora, M.2
-
28
-
-
0001497456
-
-
(Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana
-
c) R. Rossi, F. Bellina in Targets in Heterocyclic Systems: Shemistry and Properties, Vol. 5 (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, 2002, pp. 169-198.
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(2002)
Targets in Heterocyclic Systems: Shemistry and Properties
, vol.5
, pp. 169-198
-
-
Rossi, R.1
Bellina, F.2
-
29
-
-
0001227161
-
-
a) N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Angew. Chem. 2002, 114, 1065-1068; Angew. Chem. Int. Ed. 2002, 41, 1023-1026;
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(2002)
Angew. Chem.
, vol.114
, pp. 1065-1068
-
-
Furuichi, N.1
Hara, H.2
Osaki, T.3
Mori, H.4
Katsumura, S.5
-
30
-
-
0037087785
-
-
a) N. Furuichi, H. Hara, T. Osaki, H. Mori, S. Katsumura, Angew. Chem. 2002, 114, 1065-1068; Angew. Chem. Int. Ed. 2002, 41, 1023-1026;
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(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 1023-1026
-
-
-
31
-
-
8644283571
-
-
b) 1N. Furuichi, H. Hara, T. Osaki, M. Takano, H. Mori, S. Katsumura, J. Org. Chem. 2004, 69, 7949-7959.
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(2004)
J. Org. Chem.
, vol.69
, pp. 7949-7959
-
-
Furuichi, N.1
Hara, H.2
Osaki, T.3
Takano, M.4
Mori, H.5
Katsumura, S.6
-
32
-
-
37049075312
-
-
a) Synthesis of a racemic mixture of diastereomers: M. Ito, Y. Hirata, Y. Shibata, K. Tsukida, J. Chem. Soc. Perkin Trans. 1 1990, 197-199;
-
(1990)
J. Chem. Soc. Perkin Trans. 1
, pp. 197-199
-
-
Ito, M.1
Hirata, Y.2
Shibata, Y.3
Tsukida, K.4
-
38
-
-
0029896691
-
-
D. A. Nugiel, K. Jacobs, T. Worley, M. Patel, R. F. Kaltenbach III, D. T. Meyer, P. K. Jadhav, G. V. De Lucca, T. E. Smyser, R. M. Klabe, L. T. Bacheler, M. M. Rayner, S. P. Seitz, J. Med. Chem. 1996, 39, 2156-2169.
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(1996)
J. Med. Chem.
, vol.39
, pp. 2156-2169
-
-
Nugiel, D.A.1
Jacobs, K.2
Worley, T.3
Patel, M.4
Kaltenbach III, R.F.5
Meyer, D.T.6
Jadhav, P.K.7
De Lucca, G.V.8
Smyser, T.E.9
Klabe, R.M.10
Bacheler, L.T.11
Rayner, M.M.12
Seitz, S.P.13
-
39
-
-
0035855341
-
-
J. McNulty, V. Grunner, J. Mao, Tetrahedron Lett. 2001, 42, 5609-5612.
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(2001)
Tetrahedron Lett.
, vol.42
, pp. 5609-5612
-
-
McNulty, J.1
Grunner, V.2
Mao, J.3
-
40
-
-
84980173028
-
-
O. Isler, H. Gutmann, M. Montavon, R. Rüegg, G. Ryser, P. Zeller, Helv. Chim. Acta 1957, 40, 1242-1249.
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(1957)
Helv. Chim. Acta
, vol.40
, pp. 1242-1249
-
-
Isler, O.1
Gutmann, H.2
Montavon, M.3
Rüegg, R.4
Ryser, G.5
Zeller, P.6
-
42
-
-
16244410073
-
-
note
-
13C NMR spectra and correct combustion analyses, except aldehyde 21, (hydroxyalkyl)butenolides 35, 4, and 5, and the unstable alkylidenebutenolides 36 and 37; all of these, however, provided correct high-resolution mass spectra.
-
-
-
-
43
-
-
16244385562
-
-
note
-
2Et gave the ethyl ester/Weinreb amide analogue of 17 as an E:Z mixture (93% yield, E:Z = 59:41).
-
-
-
-
44
-
-
0002714675
-
-
W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2923-2925
-
-
Still, W.C.1
Kahn, M.2
Mitra, A.3
-
45
-
-
16244406496
-
-
note
-
2Et gave all four diene stereoisomers of the ethyl ester/Weinreb amide analogue of 18 in a combined yield of 49%.
-
-
-
-
47
-
-
0034725908
-
-
and references therein
-
K. Ando, T. Oishi, M. Hirama, H. Ohno, T. Ibuka, J. Org. Chem. 2000, 65, 4745-4749, and references therein.
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J. Org. Chem.
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, pp. 4745-4749
-
-
Ando, K.1
Oishi, T.2
Hirama, M.3
Ohno, H.4
Ibuka, T.5
-
50
-
-
0035925006
-
-
B. S. Crombie, C. Smith, C. Z. Varnavas, T. W. Wallace, J. Chem. Soc. Perkin Trans. 1 2001, 206-215.
-
(2001)
J. Chem. Soc. Perkin Trans. 1
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-
-
Crombie, B.S.1
Smith, C.2
Varnavas, C.Z.3
Wallace, T.W.4
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52
-
-
85064561059
-
-
b) A. Abad, C. Agulló, M. Arnó, A. C. Cuñat, R. Zaragozá, Synlett 1993, 895-896;
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(1993)
Synlett
, pp. 895-896
-
-
Abad, A.1
Agulló, C.2
Arnó, M.3
Cuñat, A.C.4
Zaragozá, R.5
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53
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-
0034223238
-
-
c) R. Okazaki, H. Kiyota, T. Oritani, Biosci. Biotechnol. Biochem. 2000, 64, 1444-1447.
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(2000)
Biosci. Biotechnol. Biochem.
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Okazaki, R.1
Kiyota, H.2
Oritani, T.3
-
56
-
-
16244417108
-
-
note
-
H(B),117Sn = 71.7 Hz; A: 1-H, B: 2-H).
-
-
-
-
57
-
-
16244385234
-
-
Dissertation, Universität Freiburg
-
3SnH; epoxidation with meta-chloroperbenzoic acid: F. v. d. Ohe, Dissertation, Universität Freiburg, 2001.
-
(2001)
-
-
Ohe, F.V.D.1
-
58
-
-
16244375814
-
-
note
-
4′,3′ = 11.5 Hz, 4′-H).
-
-
-
-
59
-
-
0000802361
-
-
V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652.
-
(1997)
Org. React.
, vol.50
, pp. 1-652
-
-
Farina, V.1
Krishnamurthy, V.2
Scott, W.J.3
-
62
-
-
16244416465
-
-
note
-
4‴,3‴ = 11.5 Hz, 4‴-H).
-
-
-
-
63
-
-
16244403565
-
-
note
-
6) data see Scheme 6.
-
-
-
-
64
-
-
16244415475
-
-
note
-
3 (71% yield). In the same way, when we processed the aldehyde analogue of the ester-substituted bromobutenolide 35, we could swap the steps, i.e., start with the elimination and couple with the (4S)-4-hydroxy analogue of trans-31. The detailed results will be reported in a full paper.
-
-
-
|