-
3
-
-
34250723953
-
-
CCDC-635769)
-
(c) Tang, J.; Li, H.-L.; Shen, Y.-H.; Jin, H.-Z.; Yan, S.-K.; Liu, R.-H.; Zhang, W.-D. Helv. Chim. Acta 2007, 90, 769 (CCDC-635769).
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Helv. Chim. Acta
, vol.90
, pp. 769
-
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Tang, J.1
Li, H.-L.2
Shen, Y.-H.3
Jin, H.-Z.4
Yan, S.-K.5
Liu, R.-H.6
Zhang, W.-D.7
-
5
-
-
85023563703
-
-
(b) Renforado, J. M.; Flacke, W.; Swaine, C. R.; Mosimann, W. J. Pharmacol. Exp. Ther. 1960, 130, 311.
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Pharmacol. Exp. Ther
, vol.130
, pp. 311
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Renforado, J.M.1
Flacke, W.2
Swaine, C.R.3
Mosimann, W.J.4
-
7
-
-
85032626828
-
-
The equilibrium between hemiketal=hydroxy ketone reduced the number of asymmetric centers to 15 in (+)-germine. Our interest was in the synthesis of the (±)-germine derivative rather than the (+)-isomer, reducing the relative asymmetric center from 15 to 14
-
The equilibrium between hemiketal=hydroxy ketone reduced the number of asymmetric centers to 15 in (+)-germine. Our interest was in the synthesis of the (±)-germine derivative rather than the (+)-isomer, reducing the relative asymmetric center from 15 to 14.
-
-
-
-
8
-
-
0000756322
-
-
Stork, G.; Meisels, A.; Davies, J. E. J. Am. Chem. Soc. 1963, 85, 3419.
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(1963)
J. Am. Chem. Soc
, vol.85
, pp. 3419
-
-
Stork, G.1
Meisels, A.2
Davies, J.E.3
-
9
-
-
0000075238
-
-
Kabalka, G. W.; Yang, D. T. C.; Baker, J. D. J. Org. Chem. 1976, 41, 574.
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(1976)
J. Org. Chem
, vol.41
, pp. 574
-
-
Kabalka, G.W.1
Yang, D.T.C.2
Baker, J.D.3
-
10
-
-
0016030007
-
-
Compound 4 was previously observed in the mixture of products from the degradation of abietic acid: Wirthlin, T.; Wehrli, H.; Jeger, O. Helv. Chim. Acta 1974, 57, 351.
-
(1974)
Helv. Chim. Acta
, vol.57
, pp. 351
-
-
Wirthlin, T.1
Wehrli, H.2
Jeger, O.3
-
11
-
-
85032636728
-
-
Epoxidation from the α-face of the olefin in 4 is favored due to a steric hindrance from the angular methyl group at the C10, blocking the β-face (more than a steric hindrance from the C6 methylene group on the α-face of the olefin)
-
Epoxidation from the α-face of the olefin in 4 is favored due to a steric hindrance from the angular methyl group at the C10, blocking the β-face (more than a steric hindrance from the C6 methylene group on the α-face of the olefin).
-
-
-
-
12
-
-
85032631745
-
-
Treatment with either lithium diethylamide in THF or aluminum tert-butoxide in refluxing toluene, undesired α-expoxide 5α can be opened to give the undesired α-allylic alcohol (an epimer of 6). Further treatment of the undesired α-allylic alcohol with Al(iPrO) 3 (m-xylene, 135 °C) equilibrates to the desired more stable β-allylic alcohol 6 (1:4 = α/β). Further heating did not alter the ratio. Thus, a mixture of 5α and 5β was treated directly with Al(iPrO)3 in boiling m-xylene
-
Treatment with either lithium diethylamide in THF or aluminum tert-butoxide in refluxing toluene, undesired α-expoxide 5α can be opened to give the undesired α-allylic alcohol (an epimer of 6). Further treatment of the undesired α-allylic alcohol with Al(iPrO)3 (m-xylene, 135 °C) equilibrates to the desired more stable β-allylic alcohol 6 (1:4 = α/β). Further heating did not alter the ratio. Thus, a mixture of 5α and 5β was treated directly with Al(iPrO)3 in boiling m-xylene.
-
-
-
-
13
-
-
33947459956
-
-
(a) Dauben, W. G.; Fonken, G. J.; Noyce, D. S. J. Am. Chem. Soc. 1956, 78, 2579.
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(1956)
J. Am. Chem. Soc
, vol.78
, pp. 2579
-
-
Dauben, W.G.1
Fonken, G.J.2
Noyce, D.S.3
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15
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-
49549130554
-
-
Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973.
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(1976)
Tetrahedron Lett
, vol.17
, pp. 1973
-
-
Van Rheenen, V.1
Kelly, R.C.2
Cha, D.Y.3
-
17
-
-
34047148768
-
-
(a) Hata, K.; Hamamoto, H.; Shiozaki, Y.; Cämmerer, S. B.; Kita, Y. Tetrahedron 2007, 63, 4052.
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(2007)
Tetrahedron
, vol.63
, pp. 4052
-
-
Hata, K.1
Hamamoto, H.2
Shiozaki, Y.3
Cämmerer, S.B.4
Kita, Y.5
-
23
-
-
85032646037
-
-
We also made 21 by a different route: sodium borohydride, then benzoyl chloride on the aldehyde 20, in which the ring A glycol had been deprotected and transformed into a mono-p-methoxybenzyl ether. See the SI for the conversion of 20 to 21
-
We also made 21 by a different route: sodium borohydride, then benzoyl chloride on the aldehyde 20, in which the ring A glycol had been deprotected and transformed into a mono-p-methoxybenzyl ether. See the SI for the conversion of 20 to 21.
-
-
-
-
24
-
-
0003282687
-
-
(E/Z = 2.5/1)
-
(a) Mandai, T.; Osaka, K.; Wada, T.; Kawada, M.; Otera, J. Tetrahedron Lett. 1983, 24, 1171 (E/Z = 2.5/1).
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(1983)
Tetrahedron Lett
, vol.24
, pp. 1171
-
-
Mandai, T.1
Osaka, K.2
Wada, T.3
Kawada, M.4
Otera, J.5
-
25
-
-
0001074970
-
-
This paper is perhaps the most relevant: it makes conjugated alkoxydienes via triphenylphosphoranes and obtains the dienes in an E/Z ratio of 2.5: 1
-
(b) Mandai, T.; Osaka, K.; Kawagishi, M.; Kawada, M.; Otera, J. J. Org. Chem. 1984, 49, 3595. This paper is perhaps the most relevant: it makes conjugated alkoxydienes via triphenylphosphoranes and obtains the dienes in an E/Z ratio of 2.5:1.
-
(1984)
J. Org. Chem
, vol.49
, pp. 3595
-
-
Mandai, T.1
Osaka, K.2
Kawagishi, M.3
Kawada, M.4
Otera, J.5
-
26
-
-
53649101963
-
-
(E/Z = 5/2)
-
(c) Ikeda, S.; Shibuya, M.; Kanoh, N.; Iwabuchi, Y. Chem. Lett. 2008, 37, 962 (E/Z = 5/2).
-
(2008)
Chem. Lett
, vol.37
, pp. 962
-
-
Ikeda, S.1
Shibuya, M.2
Kanoh, N.3
Iwabuchi, Y.4
-
28
-
-
37049106505
-
-
(e) Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1979, 3099.
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(1979)
J. Chem. Soc. Perkin Trans
, vol.1
, pp. 3099
-
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Earnshaw, C.1
Wallis, C.J.2
Warren, S.3
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29
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-
0000252132
-
-
(a) McDougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condon, B. J. Org. Chem. 1986, 51, 3388.
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(1986)
J. Org. Chem
, vol.51
, pp. 3388
-
-
McDougal, P.G.1
Rico, J.G.2
Oh, Y.-I.3
Condon, B.4
-
30
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-
0025364121
-
-
We made this compound, originally, by ozonolysis of the bis TBS derivative of cis 1, 4-butenediol
-
(b) Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579. We made this compound, originally, by ozonolysis of the bis TBS derivative of cis 1, 4-butenediol.
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(1990)
Tetrahedron
, vol.46
, pp. 1579
-
-
Aszodi, J.1
Bonnet, A.2
Teutsch, G.3
-
32
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-
85032636368
-
-
The stereochemistry of 27b was confirmed by X-ray analysis of the derivative 35. See the SI for the conversion of 27b to 35
-
The stereochemistry of 27b was confirmed by X-ray analysis of the derivative 35. See the SI for the conversion of 27b to 35.
-
-
-
-
33
-
-
33845278128
-
-
Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
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(1988)
J. Am. Chem. Soc
, vol.110
, pp. 3588
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-
Maruoka, K.1
Itoh, T.2
Sakurai, M.3
Nonoshita, K.4
Yamamoto, H.5
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34
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-
84856637775
-
-
Chini, M. G.; Jones, C. R.; Zampella, A.;D'Auria, M. V.; Renga, B.; Fiorucci, S.; Butts, C. P.; Bifulco, G. J. Org. Chem. 2012, 77, 1489.
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(2012)
J. Org. Chem
, vol.77
, pp. 1489
-
-
Chini, M.G.1
Jones, C.R.2
Zampella, A.3
D'Auria, M.V.4
Renga, B.5
Fiorucci, S.6
Butts, C.P.7
Bifulco, G.8
-
35
-
-
0032508065
-
-
A plan for conversion of 33a to 1 was (with various deprotections/protections) C4-CH2OH to C4-CO2H, followed by Barton's conditions to change C4-CO2H to C4-OH. Barton, D. H. R.; Gero, S. D.; Holliday, P.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron 1998, 54, 6751.
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(1998)
Tetrahedron
, vol.54
, pp. 6751
-
-
Barton, D.H.R.1
Gero, S.D.2
Holliday, P.3
Quiclet-Sire, B.4
Zard, S.Z.5
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