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1
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For recent excellent reviews on the clerodane diterpenoids and related compounds including marine natural products, see: (a) Tokoroyama, T. Synthesis 2000, 611-623; (b) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, 1995; Vol. 15, pp. 289-326.
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Tokoroyama, T.1
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77957087867
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Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam
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For recent excellent reviews on the clerodane diterpenoids and related compounds including marine natural products, see: (a) Tokoroyama, T. Synthesis 2000, 611-623; (b) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, 1995; Vol. 15, pp. 289-326.
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Capon, R.J.1
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(Harbor Branch Oceanographics Institution, Inc., USA). PCT WO 9112250 A1, August 22, 1991
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Wright, A. E.; Cross, S. S.; Burres, N. S.; Koehn, F. (Harbor Branch Oceanographics Institution, Inc., USA). PCT WO 9112250 A1, August 22, 1991.
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Wright, A.E.1
Cross, S.S.2
Burres, N.S.3
Koehn, F.4
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6
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0005165989
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note
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It was reported that aureol (1) was isolated in 0.036% yield (dry weight) from the marine sponge Smenospongia aurea, see Ref. 2.
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10
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0035965756
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Quite recently, Waldmann et al. reported an analogous rearrangement reaction in their total synthesis of nakijiquinones, novel marine sesquiterpene quinones. In this work, the rearrangement products related to 1 and 3 were regarded as undesired and useless compounds; hence, a detailed description including the stereoselectivity, yield, and reaction conditions for this rearrangement was not provided. See: Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586-11593.
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Stahl, P.1
Kissau, L.2
Mazitschek, R.3
Huwe, A.4
Furet, P.5
Giannis, A.6
Waldmann, H.7
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11
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Lakshmi V., Gunasekera S.P., Schmitz F.J., Ji X., van der Helm D. J. Org. Chem. 55:1990;4709-4711.
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Lakshmi, V.1
Gunasekera, S.P.2
Schmitz, F.J.3
Ji, X.4
Van der Helm, D.5
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13
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0034714389
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Recently, we noticed that Kobayashi and co-workers also encountered similar CAN oxidation problems in their synthetic studies on akaterpin, a novel marine natural product, see: Kawai N., Fujibayashi Y., Kuwabara S., Takao K., Ijuin Y., Kobayashi S. Tetrahedron. 56:2000;6467-6478.
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Kawai, N.1
Fujibayashi, Y.2
Kuwabara, S.3
Takao, K.4
Ijuin, Y.5
Kobayashi, S.6
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Katoh T., Nakatani M., Shikita S., Sampe R., Ishiwata A., Ohmori O., Nakamura M., Terashima S. Org. Lett. 3:2001;2701-2704.
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Katoh, T.1
Nakatani, M.2
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Nakamura, M.7
Terashima, S.8
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Saito N., Obara Y., Aihara T., Harada S., Shida Y., Kubo A. Tetrahedron. 50:1994;3915-3928.
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Yeh, W.-L.5
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26
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0005161869
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note
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To obtain theoretical support for the rearrangement/cyclization event, we carried out computational studies with Gaussian 98 program ( Ref. 17 ). The structural optimizations of the compounds 1 and 3 were carried out by the B3LYP DFT (density functional theory) using 6-31G(D) as a basis set. The calculations estimate that the trans-fused decalin compound 3 is 6.67 kcal/mol more stable than aureol (1) possessing the cis-fused decalin system.
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27
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0003662632
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M., Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Guassian 98, Revision A.9; Guassian, Inc.: Pittsburgh PA, 1998.
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Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery J.A., Jr.8
Stratmann, R.E.9
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Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Salvador, P.30
Dannenberg, J.J.31
Malick, D.K.32
Rabuck, A.D.33
Raghavachari, K.34
Foresman, J.B.35
Cioslowski, J.36
Ortiz, J.V.37
Baboul, A.G.38
Stefanov, B.B.39
Liu, G.40
Liashenko, A.41
Piskorz, P.42
Komaromi, I.43
Gomperts, R.44
Martin, R.L.45
Fox, D.J.46
Keith, T.47
Al-Laham, M.A.48
Peng, C.Y.49
Nanayakkara, A.50
Challacombe, M.51
Gill, P.M.W.52
Johnson, B.53
Chen, W.54
Wong, M.W.55
Andres, J.L.56
Gonzalez, C.57
Head-Gordon, M.58
Replogle, E.S.59
Pople, J.A.60
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