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Scheuer, P. J, Ed, Academic Press: New York, Chap. 2
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(c) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1978, Chap. 2.
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(d) Jaenicke, L.; Boland, W. Angew. Chem., Int. Ed. Engl. 1982, 21, 643.
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(a) Moore, R. E.; Petrus, J. A. Jr.; Doty, M. S. Tetrahedron Lett. 1968, 9, 4787.
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(d) Moore, R. E.; Pettus, J. A. Jr.; Mistysyn, J. J. Org. Chem. 1974, 39, 2201.
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(e) Moore, R. E. Lloydia 1976, 39, 181.
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Lloydia
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Moore, R.E.1
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(g) Müller, D. G.; Gassmann, G.; Boland, W.; Marnek, F.; Jaenicke, L. Science 1981, 212, 1040.
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Müller, D.G.1
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Jaenicke, L.5
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(h) Müller, D. G.; Clayton, M. N.; Gassmann, G.; Boland, W.; Marner, F.-J.; Jaenicke, L. Experientia 1984, 40, 211.
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Müller, D.G.1
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Marner, F.-J.5
Jaenicke, L.6
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13
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(i) Müller, D. G.; Clayton, M. N.; Gassmann, G.; Boland, W.; Marner, F.-J.; Schotten, T.; Jaenicke, L. Naturwissenschaften 1985, 72, 97.
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Naturwissenschaften
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Müller, D.G.1
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Schotten, T.6
Jaenicke, L.7
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16
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0001518426
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(l) Kajiwara, T.; Hatanaka, A.; Tahala, Y.; Kawai, T.; Ishihara, M.; Tsuneya, T.; Fujimura, T. Phytochemistry 1989, 28, 636.
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Kajiwara, T.1
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Tahala, Y.3
Kawai, T.4
Ishihara, M.5
Tsuneya, T.6
Fujimura, T.7
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17
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0008325606
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(m) Kajiwara, T.; Hatanaka, A.; Kodama, K.; Ochi, S.; Fujimura, T. Phytochemistry 1991, 30, 1805.
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Kajiwara, T.1
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Ochi, S.4
Fujimura, T.5
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18
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84987566206
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(n) Wirth, D.; Fischer-Lui, I.; Boland, W.; Icheln, D.; Runge, T.; König, W. A.; Philips, J.; Clayton, M. Helv. Chim. Acta 1992, 75, 734.
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Wirth, D.1
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Icheln, D.4
Runge, T.5
König, W.A.6
Philips, J.7
Clayton, M.8
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20
-
-
42949113187
-
-
Later, (1S,2S)-dictyopterene B enantiomer was discovered us a minor component in female gametes and essential oils of families Scytosiphonaceae, Chordariaceae, Dictyotaceae, see ref. 2m.
-
Later, (1S,2S)-dictyopterene B enantiomer was discovered us a minor component in female gametes and essential oils of families Scytosiphonaceae, Chordariaceae, Dictyotaceae, see ref. 2m.
-
-
-
-
21
-
-
85004559875
-
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Optically pure dictyopterene A: (a) Kajiwara, T.; Nakatomi, T.; Sasaki, Y.; Hatanaka, A. Agric. Biol. Chem. 1980, 44, 2099.
-
Optically pure dictyopterene A: (a) Kajiwara, T.; Nakatomi, T.; Sasaki, Y.; Hatanaka, A. Agric. Biol. Chem. 1980, 44, 2099.
-
-
-
-
22
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0542389124
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(b) Schotten, T.; Boland, W.; Jaenicke, L. Helv. Chim. Acta 1985, 68, 1186.
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Schotten, T.1
Boland, W.2
Jaenicke, L.3
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23
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0026021948
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(c) Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215.
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Grandjean, D.1
Pale, P.2
Chuche, J.3
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25
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0027407464
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(e) Narjes, F.; Bolte, O.; Icheln, D.; König, W. A.; Schaumann, E. J. Org. Chem. 1993, 58, 626.
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J. Org. Chem
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Narjes, F.1
Bolte, O.2
Icheln, D.3
König, W.A.4
Schaumann, E.5
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26
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0034088935
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(f) Itoh, T.; Inoue, H.; Emoto, S. Bull. Chem. Soc. Jpn. 2000, 73, 409.
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Bull. Chem. Soc. Jpn
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Itoh, T.1
Inoue, H.2
Emoto, S.3
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27
-
-
42949127750
-
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Optically pure dictyopterene B: Dorch, D.; Kunz, E.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3319; and ref. 4a,b.
-
Optically pure dictyopterene B: Dorch, D.; Kunz, E.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3319; and ref. 4a,b.
-
-
-
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28
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0001162575
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Selected examples: (a) Yamada, K.; Tan, H.; Hirota, K. Tetrahedron Lett. 1980, 21, 4873.
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Selected examples: (a) Yamada, K.; Tan, H.; Hirota, K. Tetrahedron Lett. 1980, 21, 4873.
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30
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37049135018
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(c) Billups, W. E.; Chow, W. Y.; Gross, J. H. J. Chem. Soc., Chem. Commun. 1974, 252.
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Billups, W.E.1
Chow, W.Y.2
Gross, J.H.3
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38
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0037547123
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Thematic issue on cyclopropane chemistry (guest editor: A. de Meijere): Chem. Rev. 2002, 103, 931-1647.
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Thematic issue on cyclopropane chemistry (guest editor: A. de Meijere): Chem. Rev. 2002, 103, 931-1647.
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43
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(b) Garcia, P. G.; Hohn, E.; Pietruszka, J. J. Organomet. Chem. 2003, 680, 281.
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Garcia, P.G.1
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(a) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
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Chatterjee, A.K.1
Choi, T.-L.2
Sanders, D.P.3
Grubbs, R.H.4
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46
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0034639441
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(b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58.
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Blackwell, H.E.1
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Chatterjee, A.K.3
Washenfelder, R.A.4
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Grubbs, R.H.6
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47
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84981772814
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(a) Schlosser, M.; Christmann, K. F. Angew. Chem., Int. Ed. Engl. 1966, 5, 126.
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Angew. Chem., Int. Ed. Engl
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Schlosser, M.1
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(b) Schlosser, M.; Tuong, H. B.; Schaub, B. Tetrahedron Lett. 1985, 26, 311.
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Tetrahedron Lett
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Schlosser, M.1
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0001465652
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(b) Blakemore, P. R.; Kocienski, P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans. 1 1999, 955.
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Blakemore, P.R.1
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Muir, K.4
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(c) Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26.
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Synlett
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Blakemore, P.R.1
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52
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(d) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
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Synthesis
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Bellingham, R.1
Jarowicki, K.2
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53
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42949143247
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Representative Procedure, Synthesis of E-olefin 6 To a stirred solution of the sulfone 7 (0.08 g, 0.28 mmol, 1.5 equiv) in anhyd DME (4 mL) at -60°C under N2 was added dropwise via cannula a solution of KHMDS (0.07 g, 0.34 mmol, 1.8 equiv) in anhyd DME (2 mL) over 5 min. The yellow-orange solution was stirred for 5 min and the aldehyde 3 (0.1 g, 0.19 mmol, 1 equiv) in anhyd DME (2 mL) was added dropwise via cannula over 5 min. The reaction mixture was stirred additional 10 min at -60°C and was then quenched with H2O (1 mL, The mixture was stirred vigorously whilst warming to r.t, diluted with Et2O (4 mL) and H2O (4 mL, and finally extracted with Et2O (3 x 4 mL, The combined organic layers were dried (MgSO4, filtered, and concentrated under reduced pressure. The crude product 6 was purified by flash column chromatography SiO2, petroleum ether-EtOAc, 95
-
ipso).
-
-
-
-
54
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33751155775
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(a) Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
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(1995)
J. Org. Chem
, vol.60
, pp. 3020
-
-
Vedejs, E.1
Chapman, R.W.2
Fields, S.C.3
Lin, S.4
Schrimpf, M.R.5
-
58
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-
0037128484
-
-
Published racemate of oxaborinane 9: Markó, I. E.; Giard, T.; Sumida, S.; Gies, A.-E. Tetrahedron Lett. 2002, 43, 2317.
-
Published racemate of oxaborinane 9: Markó, I. E.; Giard, T.; Sumida, S.; Gies, A.-E. Tetrahedron Lett. 2002, 43, 2317.
-
-
-
-
62
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42949132334
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-
1S,2S)-Dictyopterene A (1, α] D20 -69.3 (c 0.40, CHCl3, ref. 2d: [α]D22 +72 (c 6.74, CHCl3) for the 1R,2R-enantiomer. GC-MS (EI, 70 eV, m/z, 150 (100, M, 135 (15, M, CH3, 122 (24, M, C 2H4, 121 (60, M, C2H 5, 1H NMR (600 MHz, CDCl3, δ, 0.75-0.84 (m, 2 H, 3′-H, 0.87 (t, 3J 5″,6″, 7.0 Hz, 3 H, 6″-H, 1.25-1.35 (m, 4 H, 4″ and 5″-H, 1.36-1.41 (m, 2 H, 1′-H and 2′-H, 1.95-2.05 (m, 2 H, 3″-H, 4.84 (dd, 3J1,2, 10.2 Hz, 2J2a,2b, 2.3 Hz, 1 H, 2-Ha, 4.98 dd, 3J1,2, 17.2 Hz, 2 J2a,2b, 2.3 Hz
-
3): δ = 14.1 (C-6″), 14.8 (C-3′), 22.3 (C-5″), 23.6 (C-2′), 24.3 (C-1′), 31.8 (C-4″), 32.2 (C-3″), 111.8 (C-2), 129.2 (C-2″), 131.6 (C-1″), 140.9 (C-1).
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