-
1
-
-
0028910985
-
-
(a) Patil, A. D.; Kumar, N. V.; Kokke, W. C., Bean, M. F.; Freyer, A. J.; De Brosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182-1188.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1182-1188
-
-
Patil, A.D.1
Kumar, N.V.2
Kokke, W.C.3
Bean, M.F.4
Freyer, A.J.5
De Brosse, C.6
Mai, S.7
Truneh, A.8
Faulkner, D.J.9
Carte, B.10
Breen, A.L.11
Hertzberg, R.P.12
Johnson, R.K.13
Westley, J.W.14
Potts, B.C.M.15
-
2
-
-
0030995278
-
-
(b) Patil, A. D.; Freyer, A. J.; Taylor, P. B.; Carté, B.; Zuber, G.; Johnson, R. K.; Faulkner, D. J. J. Org. Chem. 1997, 62, 1814-1819.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 1814-1819
-
-
Patil, A.D.1
Freyer, A.J.2
Taylor, P.B.3
Carté, B.4
Zuber, G.5
Johnson, R.K.6
Faulkner, D.J.7
-
3
-
-
0029069618
-
-
(a) Rao, A. V. R.; Gurjar, M. K.; Vasudevan, J. J. Chem. Soc., Chem. Commun. 1995, 1369-1370.
-
(1995)
J. Chem. Soc., Chem. Commun.
, pp. 1369-1370
-
-
Rao, A.V.R.1
Gurjar, M.K.2
Vasudevan, J.3
-
4
-
-
0030068299
-
-
(b) Louwrier, S.; Ostendorf, M.; Tuynman, A.; Hiemstra, H. Tetrahedron Lett. 1996, 37, 905-908.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 905-908
-
-
Louwrier, S.1
Ostendorf, M.2
Tuynman, A.3
Hiemstra, H.4
-
5
-
-
0030590453
-
-
(c) Black, G. P.; Murphy, P. J.; Walshe, N. D. A.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A. Tetrahedron Lett. 1996, 37, 6943-6946.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 6943-6946
-
-
Black, G.P.1
Murphy, P.J.2
Walshe, N.D.A.3
Hibbs, D.E.4
Hursthouse, M.B.5
Malik, K.M.A.6
-
8
-
-
0032491029
-
-
(f) Black, G. P.; Murphy, P. J.; Walshe, N. D. A. Tetrahedron 1998, 54, 9481-9488.
-
(1998)
Tetrahedron
, vol.54
, pp. 9481-9488
-
-
Black, G.P.1
Murphy, P.J.2
Walshe, N.D.A.3
-
9
-
-
0033525821
-
-
(g) Franklin, A. S.; Ly, S. K.; Mackin, G. H.; Overman, L. E.; Shaka, A. J. J. Org. Chem. 1999, 64, 1512-1519.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1512-1519
-
-
Franklin, A.S.1
Ly, S.K.2
Mackin, G.H.3
Overman, L.E.4
Shaka, A.J.5
-
11
-
-
0033619847
-
-
(i) Cohen, F.; Overman, L. E.; Sakata, S. K. L. Org. Lett. 1999, 1, 2169-2172.
-
(1999)
Org. Lett.
, vol.1
, pp. 2169-2172
-
-
Cohen, F.1
Overman, L.E.2
Sakata, S.K.L.3
-
13
-
-
0033591151
-
-
(k) Black, G. P.; Murphy, P. J.; Thornhill, A. J.; Walshe, N. D. A.; Zanetti, C. Tetrahedron 1999, 55, 6547-6554.
-
(1999)
Tetrahedron
, vol.55
, pp. 6547-6554
-
-
Black, G.P.1
Murphy, P.J.2
Thornhill, A.J.3
Walshe, N.D.A.4
Zanetti, C.5
-
14
-
-
0025187524
-
-
(a) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Hallenga, K.; Ottinger, R.; Bruno, I.; Riccio, R. Tetrahedron Lett. 1990, 31, 6531-6534.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 6531-6534
-
-
Berlinck, R.G.S.1
Braekman, J.C.2
Daloze, D.3
Hallenga, K.4
Ottinger, R.5
Bruno, I.6
Riccio, R.7
-
15
-
-
0026749873
-
-
(b) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Rogeau, D.; Amade, P. J. Nat. Prod. 1992, 55, 528-532.
-
(1992)
J. Nat. Prod.
, vol.55
, pp. 528-532
-
-
Berlinck, R.G.S.1
Braekman, J.C.2
Daloze, D.3
Bruno, I.4
Riccio, R.5
Rogeau, D.6
Amade, P.7
-
16
-
-
0027745802
-
-
(c) Jares-Erijman, E. A.; Ingrum, A. A.; Sun, F.; Rinehart, K. L. J. Nat. Prod. 1993, 56, 2186-2188.
-
(1993)
J. Nat. Prod.
, vol.56
, pp. 2186-2188
-
-
Jares-Erijman, E.A.1
Ingrum, A.A.2
Sun, F.3
Rinehart, K.L.4
-
17
-
-
0026535626
-
-
The bicyclic guanidine portion of 1 is virtually identical to crambescin/ crambine A, which has an 11-carbon saturated alkyl side chain. For a biomimetic synthesis of racemic crambescins/crambines, see: (a) Snider, B. B.; Shi, Z. J. Org. Chem. 1992, 57, 2526-2528.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 2526-2528
-
-
Snider, B.B.1
Shi, Z.2
-
19
-
-
0041705558
-
-
note
-
Carbon number labeling is in accordance with the original isolation paper (ref 1a).
-
-
-
-
20
-
-
0022448317
-
-
McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 4943-4952
-
-
McGarvey, G.J.1
Williams, J.M.2
Hiner, R.N.3
Matsubara, Y.4
Oh, T.5
-
21
-
-
0027744195
-
-
α-Bromination to form 7 proceeded via a modification of the reported procedure (Hanessian, S.; Vanasse, B.; Yang, H.; Alpegiani, M. Can. J. Chem. 1993, 71, 1407-1411) in order to minimize unwanted α-dibromination (see Supporting Information).
-
(1993)
Can. J. Chem.
, vol.71
, pp. 1407-1411
-
-
Hanessian, S.1
Vanasse, B.2
Yang, H.3
Alpegiani, M.4
-
22
-
-
84987288476
-
-
(a) Roth, M.; Dubs, P.; Gotschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710-734.
-
(1971)
Helv. Chim. Acta
, vol.54
, pp. 710-734
-
-
Roth, M.1
Dubs, P.2
Gotschi, E.3
Eschenmoser, A.4
-
23
-
-
0028130025
-
-
(b) Marchand, P.; Bellassoued, M.-C.; Lhommet, G. Synth. Commun. 1994, 24, 2577-2584.
-
(1994)
Synth. Commun.
, vol.24
, pp. 2577-2584
-
-
Marchand, P.1
Bellassoued, M.-C.2
Lhommet, G.3
-
24
-
-
0043208321
-
-
note
-
It is likely that treatment of 9E/Z with 2.2 equiv of NaH led to formation of the E-dianion, which underwent efficient cyclic urea formation.
-
-
-
-
25
-
-
0041705556
-
-
note
-
The use of 5 equiv of NaH for urea formation led to an increase in the isolated yield of the urea 10, although partial racemization led to the formation of a 3:1 mixture of enantiomers as evidenced by Mosher ester analysis of intermediate of 15. The use of 2.2 equiv of NaH minimized the extent of racemization to form 10 (er, 95:05).
-
-
-
-
26
-
-
0041705557
-
-
note
-
The use of 2,4,6-tri(tert-butyl)pyridine as an acid scavenger led to N-methylation.
-
-
-
|