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1
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For the biological activities of related labdane lactones from H. coronarium, see:. Matsuda H., Morikawa T., Sakamoto Y., Toguchida I., Yogushida I., and Yoshikawa M. Bioorg. Med. Chem. 10 (2002) 2527-2534
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Dai G.-F., Xu H.-W., Wang J.-F., Liu F.-W., and Liu H.-M. Bioorg. Med. Chem. Lett. 16 (2006) 2710-2713 and references cited therein
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33847060907
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19
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85082705352
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For alternative routes to (E)-3-(1-alkenyl)-2(5H)-furanones, see:
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For alternative routes to (E)-3-(1-alkenyl)-2(5H)-furanones, see:. Janecki T., and Bodalski R. Synthesis (1989) 506-510
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(1989)
Synthesis
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Janecki, T.1
Bodalski, R.2
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Ceñal, J.P.1
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31
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27644518812
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Tscabanenko K., Chesworth R., Parker J.S., Anand N.K., Russell A.T., Adlington R.M., and Baldwin J.E. Tetrahedron 61 (2005) 11649-11656
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34
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15444378803
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For an excellent review on misassigned natural products, see:
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For an excellent review on misassigned natural products, see:. Nicolaou K.C., and Snyder S.A. Angew. Chem., Int. Ed. 44 (2005) 1012-1044
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Nicolaou, K.C.1
Snyder, S.A.2
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40
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34848863134
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For a two-step route to these alcohols from 6 and the assignment of their C-12 stereochemistry, see Ref. 9.
-
-
-
-
42
-
-
34848815426
-
-
note
-
3): δ 172.6 (C-16), 149.6 (C-8), 142.7 (C-14), 137.1 (C-11), 129.7 (C-13), 120.8 (C-12), 108.6 (C-17), 69.8 (C-15), 54.9 (C-5), 62.4 (C-9), 42.5 (C-3), 41.0 (C-1), 33.8 (C-4), 39.5 (C-10), 37.0 (C-7), 23.6 (C-6), 33.8 (C-18), 19.3 (C-2), 22.2 (C-19),15.3 (C-20).
-
-
-
-
43
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0030965153
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The absolute configuration of co-existing labdanes has been established by synthesis:
-
The absolute configuration of co-existing labdanes has been established by synthesis:. Jung M., Lee S., and Yoon B. Tetrahedron Lett. 38 (1997) 2871-2874
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(1997)
Tetrahedron Lett.
, vol.38
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Jung, M.1
Lee, S.2
Yoon, B.3
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45
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0347026018
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Villamizar J., Fuentes J., Salazar F., Tropper E., and Alonso R. J. Nat. Prod. 66 (2003) 1623-1627
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Villamizar, J.1
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Salazar, F.3
Tropper, E.4
Alonso, R.5
-
46
-
-
34848894299
-
-
note
-
+). Found: 301.2160.
-
-
-
-
47
-
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34848814822
-
-
note
-
3): δ 6.86 (dq, J = 3.2, 1.0 Hz, 1H, H-15), 6.48 (t, J = 7.2 Hz, 1H, H-12), 5.95 (d, J = 3.4 Hz, 1H, H-14), 4.83 (dd, J = 2.8, 1.4 Hz, 1H, H-17), 4.46 (dd, J = 2.6, 1.2 Hz, 1H, H-17), 2.99 (ddd, J = 17.8, 7.0, 3.2 Hz, 1H, H-11), 2.88 (ddd, J = 17.8, 11.6, 7.9 Hz, 1H, H-11), 2.40 (ddd, J = 13.0, 4.3, 2.4 Hz, 1H), 2.01 (br dt, J = 13.0, 5.5 Hz, 2H), 1.87 (br d, J = 11.5 Hz, 1H, H-9), 1.80 (dm, J = 13.0 Hz, 1H), 1.74 (dm, J = 13.0 Hz, 1H), 0.88 (s, 3H, 18-H), 0.82 (s, 3H, 19-H), 0.76 (s, 3H, 20-H).
-
-
-
-
48
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34848855539
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A similar ratio of 3/9 (ca. 4.5:1) was obtained by starting with isomerically pure 8a. Also, exposure of 8a to 0.05 equiv of DBU in dichloromethane for 5 min at rt led to a mixture containing 3, 9 and 1.
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-
-
-
49
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0023704907
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De Bernardi M., Garlashelli L., Gatti G., Vidari G., and Vita-Finzi P. Tetrahedron 44 (1988) 235-240
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(1988)
Tetrahedron
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De Bernardi, M.1
Garlashelli, L.2
Gatti, G.3
Vidari, G.4
Vita-Finzi, P.5
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50
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34250838591
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-
After completion of this work, a substantially different, longer route to 1 from 5 (seven steps, 25% overall yield) was reported:
-
After completion of this work, a substantially different, longer route to 1 from 5 (seven steps, 25% overall yield) was reported:. Margaros I., and Vassilikogiannakis G. J. Org. Chem. 72 (2007) 4826-4831
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J. Org. Chem.
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Margaros, I.1
Vassilikogiannakis, G.2
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