-
1
-
-
0037033215
-
-
Stonik, V. A.; Kapustina, I. I.; Kalinovsky, A. I.; Dmitrenok, P. S.; Grebnev, B. B. Tetrahedron Lett. 2002, 43, 315-317.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 315-317
-
-
Stonik, V.A.1
Kapustina, I.I.2
Kalinovsky, A.I.3
Dmitrenok, P.S.4
Grebnev, B.B.5
-
2
-
-
0028333629
-
-
Venkateswarlu, Y.; Biabani, M. A. F.; Reddy, M. V. R.; Rao, T. P.; Kunwar, A. C.; Faulkner, D. J. Tetrahedron Lett. 1994, 35, 2249-2252.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2249-2252
-
-
Venkateswarlu, Y.1
Biabani, M.A.F.2
Reddy, M.V.R.3
Rao, T.P.4
Kunwar, A.C.5
Faulkner, D.J.6
-
3
-
-
0032487766
-
-
Ramesh, P.; Reddy, N. S.; Venkateswarlu, Y.; Reddy, M. V. R.; Faulkner, D. J. Tetrahedron Lett. 1998, 39, 8217-8220.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8217-8220
-
-
Ramesh, P.1
Reddy, N.S.2
Venkateswarlu, Y.3
Reddy, M.V.R.4
Faulkner, D.J.5
-
4
-
-
67649424492
-
-
Díaz-Marrero, A. R.; Porras, G.; Cueto, M.; D'Croz, L.; Lorenzo, M.; San-Martín, A.; Darias, J. Tetrahedron 2009, 65, 6029-6033.
-
(2009)
Tetrahedron
, vol.65
, pp. 6029-6033
-
-
Díaz-Marrero, A.R.1
Porras, G.2
Cueto, M.3
D'Croz, L.4
Lorenzo, M.5
San-Martín, A.6
Darias, J.7
-
5
-
-
58149331900
-
-
Grote, D.; Dahse, H.-M.; Seifert, K. Chem. Biodivers. 2008, 5, 2449-2456.
-
(2008)
Chem. Biodivers.
, vol.5
, pp. 2449-2456
-
-
Grote, D.1
Dahse, H.-M.2
Seifert, K.3
-
6
-
-
34548617201
-
-
Kamel, H. N.; Ferreira, D.; Garcia-Fernandez, L. F.; Slattery, M. J. Nat. Prod. 2007, 70, 1223-1227.
-
(2007)
J. Nat. Prod.
, vol.70
, pp. 1223-1227
-
-
Kamel, H.N.1
Ferreira, D.2
Garcia-Fernandez, L.F.3
Slattery, M.4
-
7
-
-
74849115406
-
-
Li, Y.; Pattenden, G.; Rogers, J. Tetrahedron Lett. 2010, 51, 1280-1283.
-
(2010)
Tetrahedron Lett.
, vol.51
, pp. 1280-1283
-
-
Li, Y.1
Pattenden, G.2
Rogers, J.3
-
8
-
-
41749104436
-
-
For a recent summary of cembranoid enedione natural products found in corals, see
-
For a recent summary of cembranoid enedione natural products found in corals, see: Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008, 25, 298-317;
-
(2008)
Nat. Prod. Rep.
, vol.25
, pp. 298-317
-
-
Roethle, P.A.1
Trauner, D.2
-
9
-
-
59449101761
-
-
See also
-
See also: Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2009, 26, 170-244;
-
(2009)
Nat. Prod. Rep.
, vol.26
, pp. 170-244
-
-
Blunt, J.W.1
Copp, B.R.2
Hu, W.-P.3
Munro, M.H.G.4
Northcote, P.T.5
Prinsep, M.R.6
-
10
-
-
76249124132
-
-
Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2010, 27, 165-237.
-
(2010)
Nat. Prod. Rep.
, vol.27
, pp. 165-237
-
-
Blunt, J.W.1
Copp, B.R.2
Munro, M.H.G.3
Northcote, P.T.4
Prinsep, M.R.5
-
11
-
-
0030041294
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-
Two 12-membered ring 'pseudopterane' diterpenes containing a Zalkenylbutenolide moiety are known, see
-
Two 12-membered ring 'pseudopterane' diterpenes containing a Zalkenylbutenolide moiety are known, see: Rodríguez, A. D.; Soto, J. J. Chem. Pharm. Bull. 1996, 44, 91-94;
-
(1996)
J. Chem. Pharm. Bull.
, vol.44
, pp. 91-94
-
-
Rodríguez, A.D.1
Soto, J.2
-
12
-
-
58149144599
-
-
Kate, A. S.; Aubry, I.; Tremblay, M. L.; Kerr, R. G. J. Nat. Prod. 2008, 71, 1977-1982.
-
(2008)
J. Nat. Prod.
, vol.71
, pp. 1977-1982
-
-
Kate, A.S.1
Aubry, I.2
Tremblay, M.L.3
Kerr, R.G.4
-
13
-
-
79953241545
-
-
See: (a) Refs. 2 and 8
-
See: (a) Refs. 2 and 8.;
-
-
-
-
15
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79953252944
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note
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1H NMR spectra. Interestingly, they were shown to be epimeric at the t-hydroxy centre in their cyclopentane rings, although a direct comparison has not been forthcoming; see Refs. 1 and 2. (b) In this proof-of-principle study we have used the diastereoisomer 10 of the starting material which has the same stereochemistry at the t-hydroxy centre in mandapamate, but is epimeric with the same centre in plumarellide. (c) The model compounds 8b and 8c, lacking the C-1 propenyl group present in natural cembranoids, were chosen for synthesis expediency.
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19
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0034734340
-
-
(a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8168
-
-
Garber, S.B.1
Kingsbury, J.S.2
Gray, B.L.3
Hoveyda, A.H.4
-
20
-
-
0034676688
-
-
(b) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976;
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 9973-9976
-
-
Gessler, S.1
Randl, S.2
Blechert, S.3
-
21
-
-
0043194171
-
-
(c) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 11360-11370
-
-
Chatterjee, A.K.1
Choi, T.-L.2
Sanders, D.P.3
Grubbs, R.H.4
-
22
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79953254295
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note
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3)
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23
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0035858717
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1H proton coupling data. Reference to the seminal studies of Deslongchamps et al. on the transannular Diels-Alder reaction and the predicted outcome of the sterochemistries of adducts from isomeric diene and dienophile precursors would suggest that the cis, anti, cis geometry associated with the substituted cyclohexane ring in 27 would most likely arise from the precursors 24/25 accommodating an E-dienophile. See: This analysis may be flawed however for several reasons, including the possibilities for post epimerisations of labile C-H centres in 26/27
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1H proton coupling data. Reference to the seminal studies of Deslongchamps et al. on the transannular Diels-Alder reaction and the predicted outcome of the sterochemistries of adducts from isomeric diene and dienophile precursors would suggest that the cis, anti, cis geometry associated with the substituted cyclohexane ring in 27 would most likely arise from the precursors 24/25 accommodating an E-dienophile. See: Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260. This analysis may be flawed however for several reasons, including the possibilities for post epimerisations of labile C-H centres in 26/27.
-
(2001)
Tetrahedron
, vol.57
, pp. 4243-4260
-
-
Marsault, E.1
Toró, A.2
Nowak, P.3
Deslongchamps, P.4
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26
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65349153731
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-
For recent synthetic studies with cyathane diterpenes, see
-
For recent synthetic studies with cyathane diterpenes, see: Enquist, J. A.; Stoltz, B. M. Nat. Prod. Rep. 2009, 26, 661-680.
-
(2009)
Nat. Prod. Rep.
, vol.26
, pp. 661-680
-
-
Enquist, J.A.1
Stoltz, B.M.2
-
27
-
-
0027173559
-
-
Urones, J. G.; Marcos, I. S.; Basabe, P.; Alonso, C.; Oliva, I. M.; Garrido, N. M.; Martin, D. D.; Lithgow, A. M. Tetrahedron 1993, 49, 4051-4062;
-
(1993)
Tetrahedron
, vol.49
, pp. 4051-4062
-
-
Urones, J.G.1
Marcos, I.S.2
Basabe, P.3
Alonso, C.4
Oliva, I.M.5
Garrido, N.M.6
Martin, D.D.7
Lithgow, A.M.8
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28
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0031127189
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For related homoverrucosane diterpenes, see
-
For related homoverrucosane diterpenes, see: Grammes, C.; Burkhardt, G.; Veith, M.; Huch, V.; Becker, H. Phytochemistry 1997, 44, 1495-1502.
-
(1997)
Phytochemistry
, vol.44
, pp. 1495-1502
-
-
Grammes, C.1
Burkhardt, G.2
Veith, M.3
Huch, V.4
Becker, H.5
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