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1
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(a) Kruger, G. J.; Steyn, P. S.; Vleggaar, R.; Rabie, C. J. J. Chem. Soc., Chem. Commun. 1979, 441.
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Kruger, G.J.1
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De Jesus, A.E.1
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8
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0021931895
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 231
-
-
Nishiyama, S.1
Shizuri, Y.2
Yamamura, S.3
-
9
-
-
0001360042
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 5067
-
-
Williams, D.R.1
White, F.H.2
-
10
-
-
0000499691
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 470
-
-
Suh, H.1
Wilcox, C.S.2
-
11
-
-
37049078637
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1991)
J. Chem. Soc., Perkin Trans. 1
, pp. 1947
-
-
Bowden, M.C.1
Patel, P.2
Pattenden, G.3
-
12
-
-
0013300559
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 7174
-
-
Whang, K.1
Venkataraman, H.2
Kim, Y.G.3
Cha, J.K.4
-
13
-
-
0022444095
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 3643
-
-
Nishiyama, S.1
Toshima, H.2
Kanai, H.3
Yamamura, S.4
-
14
-
-
0023793027
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 5201
-
-
Hatakeyama, S.1
Sakurai, K.2
Numata, H.3
Ochi, N.4
Takano, S.5
-
15
-
-
0025608923
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
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(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 8985
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-
Whang, K.1
Cooke, R.J.2
Okay, G.3
Cha, J.K.4
-
16
-
-
0034719252
-
-
Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
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Org. Lett.
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Hanaki, N.1
Link, J.T.2
MacMillan, D.W.C.3
Overman, L.E.4
Trankle, W.G.5
Wurster, J.A.6
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17
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0038475407
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and references therein for previous syntheses
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Synthesis of (-)-citreoviridin: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231. (b) Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067. (c) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470. (d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1947. (e) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174. Synthesis of (-)-aurovertin B: (f) Nishiyama, S.; Toshima, H.; Kanai, H.; Yamamura, S. Tetrahedron Lett. 1986, 27, 3643. Synthesis of (+)-verrucosidin: (g) Hatakeyama, S.; Sakurai, K.; Numata, H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201. (h) Whang, K.; Cooke, R. J.; Okay, G.; Cha, J. K. J. Am. Chem. Soc. 1990, 112, 8985. Synthesis of (+)-citreoviral: (i) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. (j) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2002, 4, 2945 and references therein for previous syntheses.
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Org. Lett.
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Peng, Z.-H.1
Woerpel, K.A.2
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No information is presented regarding the biosynthetic details of the key oxidative rearrangement, but insightful in vitro model studies have been reported: (a) Townsend, C. A.; Davis, S. G.; Koreeda, M.; Hulin, B. J. Org. Chem. 1985, 50, 5428. (b) Townsend, C. A.; Isomura, Y.; Davis, S. G.; Hodge, J. A. Tetrahedron 1989, 45, 2263.
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No information is presented regarding the biosynthetic details of the key oxidative rearrangement, but insightful in vitro model studies have been reported: (a) Townsend, C. A.; Davis, S. G.; Koreeda, M.; Hulin, B. J. Org. Chem. 1985, 50, 5428. (b) Townsend, C. A.; Isomura, Y.; Davis, S. G.; Hodge, J. A. Tetrahedron 1989, 45, 2263.
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1H NMR spectrum of natural (+)-asteltoxin was kindly provided by Professor Vleggaar, but unfortunately an authentic sample is no longer available due to extensive decomposition during storage.
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Two recent notable examples are Suzuki's synthesis of furaquinocins and Harran's synthesis of nominal diazonamide A featuring an epoxy alcohol rearrangement and a pinacol rearrangement, respectively: (a) Saito, T.; Suzuki, T.; Morimoto, M.; Akiyama, C.; Ochiai, T.; Takeuchi, K.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1998, 120, 11633. (b) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
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Two recent notable examples are Suzuki's synthesis of furaquinocins and Harran's synthesis of nominal diazonamide A featuring an epoxy alcohol rearrangement and a pinacol rearrangement, respectively: (a) Saito, T.; Suzuki, T.; Morimoto, M.; Akiyama, C.; Ochiai, T.; Takeuchi, K.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1998, 120, 11633. (b) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
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