-
1
-
-
0033083666
-
-
For a series of reviews covering the isolation, characterization, biological activity, and synthesis of lignans: (a) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75.
-
(1999)
Nat. Prod. Rep.
, vol.16
, pp. 75
-
-
Ward, R.S.1
-
6
-
-
0037987113
-
-
For examples of endo,exo-furofurans isolated from traditional medicines: (a) Iwakami, S.; Ebizuka, Y.; Sankawa, U. Heterocycles 1990, 30, 795.
-
(1990)
Heterocycles
, vol.30
, pp. 795
-
-
Iwakami, S.1
Ebizuka, Y.2
Sankawa, U.3
-
7
-
-
0026717837
-
-
(b) Iwakami, S.; Wu, J. B.; Ebizuka, Y.; Sankawa, U. Chem. Pharm. Bull. 1992, 40, 1196.
-
(1992)
Chem. Pharm. Bull.
, vol.40
, pp. 1196
-
-
Iwakami, S.1
Wu, J.B.2
Ebizuka, Y.3
Sankawa, U.4
-
8
-
-
0030788627
-
-
(c) Takasaki, M.; Konoshima, T.; Yasuda, I.; Hamano, T.; Tokuda, H. Biol. Pharm. Bull. 1997, 20, 776.
-
(1997)
Biol. Pharm. Bull.
, vol.20
, pp. 776
-
-
Takasaki, M.1
Konoshima, T.2
Yasuda, I.3
Hamano, T.4
Tokuda, H.5
-
9
-
-
0028255984
-
-
(d) Hashimoto, K.; Yanagisawa, T.; Okui, Y.; Ikeya, Y.; Maruno, M.; Fujita, T. Planta Med. 1994, 60, 124.
-
(1994)
Planta Med.
, vol.60
, pp. 124
-
-
Hashimoto, K.1
Yanagisawa, T.2
Okui, Y.3
Ikeya, Y.4
Maruno, M.5
Fujita, T.6
-
10
-
-
85016994417
-
-
(e) Deyama, T.; Ikawa, T.; Kitagawa, S.; Nishibe, S. Chem. Pharm. Bull. 1987, 35, 1785.
-
(1987)
Chem. Pharm. Bull.
, vol.35
, pp. 1785
-
-
Deyama, T.1
Ikawa, T.2
Kitagawa, S.3
Nishibe, S.4
-
11
-
-
0029585906
-
-
(f) Okuyama, E.; Suzumura, K.; Yamazaki, M. Chem. Pharm. Bull. 1995, 43, 2200.
-
(1995)
Chem. Pharm. Bull.
, vol.43
, pp. 2200
-
-
Okuyama, E.1
Suzumura, K.2
Yamazaki, M.3
-
12
-
-
0023005913
-
-
Ichikawa, K.; Kinoshita, T.; Nishibe, S.; Sankawa, U. Chem. Pharm. Bull. 1986, 34, 3514.
-
(1986)
Chem. Pharm. Bull.
, vol.34
, pp. 3514
-
-
Ichikawa, K.1
Kinoshita, T.2
Nishibe, S.3
Sankawa, U.4
-
13
-
-
0028208869
-
-
Chiung, Y. M.; Hayashi, H.; Matsumoto, H.; Otani, T.; Yoshida, K.; Huang, M. Y.; Chen, R. X.; Liu, J. R.; Nakayama, M. J. Antibiot. 1994, 47, 487.
-
(1994)
J. Antibiot.
, vol.47
, pp. 487
-
-
Chiung, Y.M.1
Hayashi, H.2
Matsumoto, H.3
Otani, T.4
Yoshida, K.5
Huang, M.Y.6
Chen, R.X.7
Liu, J.R.8
Nakayama, M.9
-
14
-
-
0019771885
-
-
Nikaido, T.; Ohmoto, T.; Kinoshita, T.; Sankawa, U.; Nishibe, S.; Hisada, S. Chem. Pharm. Bull. 1981, 29, 3586.
-
(1981)
Chem. Pharm. Bull.
, vol.29
, pp. 3586
-
-
Nikaido, T.1
Ohmoto, T.2
Kinoshita, T.3
Sankawa, U.4
Nishibe, S.5
Hisada, S.6
-
15
-
-
37049112551
-
-
Total synthesis of methyl xanthoxylol: (a) Pelter, A.; Ward, R. S.; Collins, P.; Venkateswarlu, R.; Kay, I. T. J. Chem. Soc., Perkin Trans. 1 1985, 587.
-
(1985)
J. Chem. Soc., Perkin Trans. 1
, pp. 587
-
-
Pelter, A.1
Ward, R.S.2
Collins, P.3
Venkateswarlu, R.4
Kay, I.T.5
-
16
-
-
0001392802
-
-
(b) Yoshida, S.; Ogiku, T.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1997, 62, 1310.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 1310
-
-
Yoshida, S.1
Ogiku, T.2
Ohmizu, H.3
Iwasaki, T.4
-
17
-
-
37049113322
-
-
(c) Total synthesis of epipinoresinol: Pelter, A.; Ward, R. S.; Watson, D. J.; Collins, P.; Kay, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 175.
-
(1982)
J. Chem. Soc., Perkin Trans. 1
, pp. 175
-
-
Pelter, A.1
Ward, R.S.2
Watson, D.J.3
Collins, P.4
Kay, I.T.5
-
18
-
-
0023851254
-
-
For various approaches to furofurans see refs 1, 6, and: (a) Takano, S.; Ohkawa, T.; Tamori, S.; Satoh, S.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 189.
-
(1988)
J. Chem. Soc., Chem. Commun.
, pp. 189
-
-
Takano, S.1
Ohkawa, T.2
Tamori, S.3
Satoh, S.4
Ogasawara, K.5
-
20
-
-
37049070735
-
-
(c) Stevens, D. R.; Till, C. P.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1992, 185.
-
(1992)
J. Chem. Soc., Perkin Trans. 1
, pp. 185
-
-
Stevens, D.R.1
Till, C.P.2
Whiting, D.A.3
-
21
-
-
0028127282
-
-
(d) van Oeveren, A.; Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1994, 59, 5999.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 5999
-
-
Van Oeveren, A.1
Jansen, J.F.G.A.2
Feringa, B.L.3
-
23
-
-
0028856166
-
-
(f) Orito, K.; Sasaki, T.; Suginome, H. J. Org. Chem. 1995, 60, 6208.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 6208
-
-
Orito, K.1
Sasaki, T.2
Suginome, H.3
-
24
-
-
0030004036
-
-
(g) Wirth, T.; Kulicke, K. J.; Fragale, G. J. Org. Chem. 1996, 61, 2686.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 2686
-
-
Wirth, T.1
Kulicke, K.J.2
Fragale, G.3
-
25
-
-
0030837529
-
-
(h) Yoshida, S.; Yamanaka, T.; Miyake, T.; Moritani, Y.; Ohmizu, H.; Iwasaki, T. Tetrahedron 1997, 53, 9585.
-
(1997)
Tetrahedron
, vol.53
, pp. 9585
-
-
Yoshida, S.1
Yamanaka, T.2
Miyake, T.3
Moritani, Y.4
Ohmizu, H.5
Iwasaki, T.6
-
26
-
-
33748615196
-
-
(i) Hull, H. M.; Jones, R. G.; Knight, D. W. J. Chem. Soc., Perkin Trans. 1 1998, 1779.
-
(1998)
J. Chem. Soc., Perkin Trans. 1
, pp. 1779
-
-
Hull, H.M.1
Jones, R.G.2
Knight, D.W.3
-
27
-
-
0034161821
-
-
(j) Ohmizu, H.; Ogiku, T.; Iwasaki, T. Heterocycles 2000, 52, 1399.
-
(2000)
Heterocycles
, vol.52
, pp. 1399
-
-
Ohmizu, H.1
Ogiku, T.2
Iwasaki, T.3
-
28
-
-
0037123610
-
-
(k) Roy, S. C.; Rana, K. K.; Guin, C. J. Org. Chem. 2002, 67, 3242.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3242
-
-
Roy, S.C.1
Rana, K.K.2
Guin, C.3
-
29
-
-
0036193542
-
-
(l) Enders, D.; Lausberg, V.; Del Signore, G.; Berner, O. M. Synthesis 2002, 515.
-
(2002)
Synthesis
, pp. 515
-
-
Enders, D.1
Lausberg, V.2
Del Signore, G.3
Berner, O.M.4
-
30
-
-
0037018490
-
-
(m) Aldous, D. J.; Dalençon, A. J.; Steel, P. G. Org. Lett. 2002, 4, 1159.
-
(2002)
Org. Lett.
, vol.4
, pp. 1159
-
-
Aldous, D.J.1
Dalençon, A.J.2
Steel, P.G.3
-
31
-
-
0037366605
-
-
Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
-
(2003)
Chem. Rev.
, vol.103
, pp. 893
-
-
Horton, D.A.1
Bourne, G.T.2
Smythe, M.L.3
-
32
-
-
0035812685
-
-
(a) Brown, R. C. D.; Bataille, C. J. R.; Bruton, G.; Hinks, J. D.; Swain, N. A. J. Org. Chem. 2001, 66, 6719.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 6719
-
-
Brown, R.C.D.1
Bataille, C.J.R.2
Bruton, G.3
Hinks, J.D.4
Swain, N.A.5
-
34
-
-
0035862690
-
-
(c) Brown, R. C. D.; Bataille, C. J. R.; Hinks, J. D. Tetrahedron Lett. 2001, 42, 473.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 473
-
-
Brown, R.C.D.1
Bataille, C.J.R.2
Hinks, J.D.3
-
35
-
-
0000302629
-
-
Ghosez has reported auxiliary-based methods for the asymmetric [242] keteniminium-olefin cycloaddition. However, in the reactions of enantiomerically enriched keteniminium salts with terminal olefins, enantioselectivities were moderate (0-76% ee): (a) Houge, C.; Frisque-Hesbain, A. M.; Mockel, A.; Ghosez, L.; Declercq, J. P.; Germain, G.; Van Meerssche, M. J. Am. Chem. Soc. 1982, 104, 2920.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 2920
-
-
Houge, C.1
Frisque-Hesbain, A.M.2
Mockel, A.3
Ghosez, L.4
Declercq, J.P.5
Germain, G.6
Van Meerssche, M.7
-
36
-
-
0037008560
-
-
(b) Ghosez, L.; Mahuteau-Betzer, F.; Genicot, C.; Vallribera, A.; Cordier, J. F. Chem.-Eur. J. 2002, 8, 3411.
-
(2002)
Chem.-Eur. J.
, vol.8
, pp. 3411
-
-
Ghosez, L.1
Mahuteau-Betzer, F.2
Genicot, C.3
Vallribera, A.4
Cordier, J.F.5
-
37
-
-
7044286458
-
-
For a review of Mn(III)-induced cyclizations: Snider, B. B. Chem. Rev. 1996, 96, 339.
-
(1996)
Chem. Rev.
, vol.96
, pp. 339
-
-
Snider, B.B.1
-
38
-
-
0024809070
-
-
For Mn(III)-mediated oxidative cyclizations to provide bicyclo-[3.1.0]lactones see: (a) Oumar-Mahamat, H.; Moustrou, C.; Surzur, J.-M. ; Bertrand, M. P. J. Org. Chem. 1989, 54, 5684.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 5684
-
-
Oumar-Mahamat, H.1
Moustrou, C.2
Surzur, J.-M.3
Bertrand, M.P.4
-
39
-
-
0242474980
-
-
(b) Oumar-Mahamat, H.; Moustrou, C.; Surzur, J.-M.; Bertrand, M. P. Tetrahedron Lett. 1989, 30, 331.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 331
-
-
Oumar-Mahamat, H.1
Moustrou, C.2
Surzur, J.-M.3
Bertrand, M.P.4
-
44
-
-
0030912922
-
-
Copper-catalyzed intramolecular cyclopropanation of the diazoderivative of 11 was also investigated, providing 12 in 42% yield as a 7:3 mixture of diastereoisomers. No further efforts were made to improve this alternative approach. For related cyclizations: Molander, G. A.; Alonso-Alija, C. Tetrahedron 1997, 53, 8067.
-
(1997)
Tetrahedron
, vol.53
, pp. 8067
-
-
Molander, G.A.1
Alonso-Alija, C.2
-
45
-
-
4243993732
-
-
Structures 27, 28, 35, 38b, and 1 were unambiguously determined by X-ray crystallography. It was also possible to confirm the absolute stereochemistry of 38b due to the presence of a heavy atom in the structure. Crystallographic data for these structures have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 219596 (28), CCDC 219598 (35), CCDC 218116 (38b), and CCDC 219597 (1). The X-ray structure of 27 has been reported previously: Gelbrich, T.; Hursthouse, M. B. Acta Crystallogr. 2001, E57, o566.
-
(2001)
Acta Crystallogr.
, vol.E57
-
-
Gelbrich, T.1
Hursthouse, M.B.2
-
46
-
-
0035825070
-
-
For an example of opening of a closely related cyclopropane using thiolate nucleophiles: Lee, C.-S.; Lee, K.-I.; Hamilton, A. D. Tetrahedron Lett. 2001, 42, 211.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 211
-
-
Lee, C.-S.1
Lee, K.-I.2
Hamilton, A.D.3
-
47
-
-
0346593077
-
-
note
-
Personal Chemistry is thanked for the donation of the Smith-Synthesizer used in this work.
-
-
-
-
48
-
-
0003573091
-
-
Van Nostrand Reinhold Company: New York
-
Although we have not experienced any problem in the handling or heating of these metal perchlorates, care should be taken when manipulating them due to their potentially explosive nature. Sax, N. I. Dangerous Properties of Industrial Materials, 5th ed.; Van Nostrand Reinhold Company: New York, 1979.
-
(1979)
Dangerous Properties of Industrial Materials, 5th Ed.
-
-
Sax, N.I.1
-
51
-
-
0001031980
-
-
(c) Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 2908
-
-
Taber, D.F.1
Herr, R.J.2
Pack, S.K.3
Geremia, J.M.4
-
52
-
-
0034714412
-
-
(d) Padwa, A.; Zhang, Z. J.; Zhi, L. J. Org. Chem. 2000, 65, 5223.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 5223
-
-
Padwa, A.1
Zhang, Z.J.2
Zhi, L.3
-
53
-
-
0000864763
-
-
3 and used in diazotransfer reactions without further purification: Reagan, M. T.; Nickon, A. J. Am. Chem. Soc. 1968, 90, 4096.
-
(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 4096
-
-
Reagan, M.T.1
Nickon, A.2
-
54
-
-
0001725065
-
-
Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 1959
-
-
Danheiser, R.L.1
Miller, R.F.2
Brisbois, R.G.3
Park, S.Z.4
-
55
-
-
0034731574
-
-
3 in diazo-transfer reactions: (a) Charette, A. B.; Wurz, R. P.; Ollevier, T. J. Org. Chem. 2000, 65, 9252.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 9252
-
-
Charette, A.B.1
Wurz, R.P.2
Ollevier, T.3
-
56
-
-
0036959639
-
-
(b) Charette, A. B.; Wurz, R. P.; Ollevier, T. Helv. Chim. Acta 2002, 85, 4468.
-
(2002)
Helv. Chim. Acta
, vol.85
, pp. 4468
-
-
Charette, A.B.1
Wurz, R.P.2
Ollevier, T.3
-
58
-
-
0033039790
-
-
(d) Benati, L.; Nanni, D.; Spagnolo, P. J. Org. Chem. 1999, 64, 5132.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5132
-
-
Benati, L.1
Nanni, D.2
Spagnolo, P.3
-
59
-
-
18444417883
-
-
For reviews of metal-catalyzed C-H insertion of diazocompounds: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919.
-
(1986)
Chem. Rev.
, vol.86
, pp. 919
-
-
Doyle, M.P.1
-
60
-
-
0001331380
-
-
Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag
-
(b) Taber, D. F. In Houben Weyl, Methods of Stereoselective Synthesis, 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E21a, pp 1127-1148.
-
(1995)
Houben Weyl, Methods of Stereoselective Synthesis, 4th Ed.
, vol.E21A
, pp. 1127-1148
-
-
Taber, D.F.1
-
62
-
-
0032544764
-
-
(d) Sulikowski, G. A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 3145
-
-
Sulikowski, G.A.1
Cha, K.L.2
Sulikowski, M.M.3
-
63
-
-
33748811198
-
-
(e) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 1797
-
-
Padwa, A.1
Austin, D.J.2
-
65
-
-
15144348175
-
-
Yonezawa, S.; Komurasaki, T.; Kawada, K.; Tsuri, T.; Fuji, M.; Kugimiya, A.; Haga, N.; Mitsumori, S.; Inagaki, M.; Nakatani, T.; Tamura, Y.; Takechi, S. ; Taishi, T.; Ohtani, M. J. Org. Chem. 1998, 63, 5831.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 5831
-
-
Yonezawa, S.1
Komurasaki, T.2
Kawada, K.3
Tsuri, T.4
Fuji, M.5
Kugimiya, A.6
Haga, N.7
Mitsumori, S.8
Inagaki, M.9
Nakatani, T.10
Tamura, Y.11
Takechi, S.12
Taishi, T.13
Ohtani, M.14
-
68
-
-
0000123148
-
-
(c) Morgan, B.; Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992, 57, 3231.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 3231
-
-
Morgan, B.1
Oehlschlager, A.C.2
Stokes, T.M.3
-
69
-
-
0345961768
-
-
note
-
R (R)-alcohol = 29.2 ruin.
-
-
-
-
70
-
-
0000270448
-
-
Isolation of(+)-xanthoxylol (1): (a) Gonzaléz, M. J. T. G.; Pinto, M. M. M.; Kijjoa, A.; Anantachoke, C.; Herz, W. Phytochemistry, 1993, 32, 433.
-
(1993)
Phytochemistry
, vol.32
, pp. 433
-
-
Gonzaléz, M.J.T.G.1
Pinto, M.M.M.2
Kijjoa, A.3
Anantachoke, C.4
Herz, W.5
-
71
-
-
0000888455
-
-
(b) Fang, J. M.; Lee, C. K.; Cheng, Y. S. Phytochemistry 1992, 31, 3659. Note that in ref 28b the structure of the wrong enantiomer is depicted. The structure of the synthetic sample of 1 prepared in our laboratory was unambiguously confirmed by X-ray crystallography (ref 16).
-
(1992)
Phytochemistry
, vol.31
, pp. 3659
-
-
Fang, J.M.1
Lee, C.K.2
Cheng, Y.S.3
-
72
-
-
44949267039
-
-
Isolation of (+)-epipinoresinol, see ref 2f and: (a) Rahman, M. M. A.; Dewick, P. M.; Jackson, D. E.; Lucas, J. A. Phytochemistry 1990, 29, 1971.
-
(1990)
Phytochemistry
, vol.29
, pp. 1971
-
-
Rahman, M.M.A.1
Dewick, P.M.2
Jackson, D.E.3
Lucas, J.A.4
-
73
-
-
0000211626
-
-
Synthesis of (±)-epipinoresinol: (b) Katayama, T.; Davin, L. B.; Chu, A.; Lewis, N. G. Phytochemistry 1993, 33, 581-591. (+)-Epipinoresinol from acid-catalyzed isomerization of (+)-pinoresinol: Nishibe, S.; Tsukamoto, H.; Hisada, S. Chem. Pharm. Bull. 1984, 32, 4653.
-
(1993)
Phytochemistry
, vol.33
, pp. 581-591
-
-
Katayama, T.1
Davin, L.B.2
Chu, A.3
Lewis, N.G.4
-
74
-
-
85009638513
-
-
Synthesis of (±)-epipinoresinol: (b) Katayama, T.; Davin, L. B.; Chu, A.; Lewis, N. G. Phytochemistry 1993, 33, 581-591. (+)-Epipinoresinol from acid-catalyzed isomerization of (+)-pinoresinol: Nishibe, S.; Tsukamoto, H.; Hisada, S. Chem. Pharm. Bull. 1984, 32, 4653.
-
(1984)
Chem. Pharm. Bull.
, vol.32
, pp. 4653
-
-
Nishibe, S.1
Tsukamoto, H.2
Hisada, S.3
-
75
-
-
0347853151
-
-
Spectroscopic data were consistent with that reported previously for methyl xanthoxylol (2): ref 6b and Bytheway, I. R.; Ghisalberti, E. L.; Gotsis, S.; Jefferies, P. R.; Skelton, B. W.; Sugars, K. E.; White, A. H. Aust. J. Chem. 1987, 40, 1913.
-
(1987)
Aust. J. Chem.
, vol.40
, pp. 1913
-
-
Bytheway, I.R.1
Ghisalberti, E.L.2
Gotsis, S.3
Jefferies, P.R.4
Skelton, B.W.5
Sugars, K.E.6
White, A.H.7
-
76
-
-
0000930101
-
-
Spectroscopic data were consistent with that reported previously for epieudesmin: (a) Chiba, M.; Hisada, S.; Nishibe, S.; Thieme, H. Phytochemistry 1980, 19, 335-336.
-
(1980)
Phytochemistry
, vol.19
, pp. 335-336
-
-
Chiba, M.1
Hisada, S.2
Nishibe, S.3
Thieme, H.4
-
77
-
-
0001646160
-
-
(b) Iida, T.; Nakano, M.; Ito, K. Phytochemistry 1982, 21, 673.
-
(1982)
Phytochemistry
, vol.21
, pp. 673
-
-
Iida, T.1
Nakano, M.2
Ito, K.3
-
78
-
-
0033804149
-
-
(c) Das, B.; Madhusudhan, P.; Venkataiah, B. Synth. Commun. 2000, 30, 4001.
-
(2000)
Synth. Commun.
, vol.30
, pp. 4001
-
-
Das, B.1
Madhusudhan, P.2
Venkataiah, B.3
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