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Volumn 125, Issue 18, 2003, Pages 5415-5421

Total synthesis of (+)-asteltoxin

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; OLEFINS; STEREOCHEMISTRY;

EID: 0038292969     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034332q     Document Type: Article
Times cited : (39)

References (84)
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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.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 231
    • Nishiyama, S.1    Shizuri, Y.2    Yamamura, S.3
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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.
    • (1987) J. Org. Chem. , vol.52 , pp. 5067
    • Williams, D.R.1    White, F.H.2
  • 10
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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.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 470
    • Suh, H.1    Wilcox, C.S.2
  • 11
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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.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 1947
    • Bowden, M.C.1    Patel, P.2    Pattenden, G.3
  • 12
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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.
    • (1991) J. Org. Chem. , vol.56 , pp. 7174
    • Whang, K.1    Venkataraman, H.2    Kim, Y.G.3    Cha, J.K.4
  • 13
    • 0022444095 scopus 로고
    • 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
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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.
    • (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
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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.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8985
    • Whang, K.1    Cooke, R.J.2    Okay, G.3    Cha, J.K.4
  • 16
    • 0034719252 scopus 로고    scopus 로고
    • 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.
    • (2000) Org. Lett. , vol.2 , pp. 223
    • Hanaki, N.1    Link, J.T.2    MacMillan, D.W.C.3    Overman, L.E.4    Trankle, W.G.5    Wurster, J.A.6
  • 17
    • 0038475407 scopus 로고    scopus 로고
    • and references therein for previous syntheses
    • 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.
    • (2002) Org. Lett. , vol.4 , pp. 2945
    • Peng, Z.-H.1    Woerpel, K.A.2
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    • For an excellent review on the biosynthesis of aflatoxins, see: (c) Minto, R. E.; Townsend, C. A. Chem. Rev. 1997, 97, 2537.
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    • Minto, R.E.1    Townsend, C.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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    • Townsend, C.A.1    Davis, S.G.2    Koreeda, M.3    Hulin, B.4
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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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    • Ph.D. Dissertation, The University of Alabama
    • Taken in part from the following: (b) Kim, H. Ph.D. Dissertation, The University of Alabama, 1997.
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    • (c) Eom, K. D. Ph.D. Dissertation, The University of Alabama, December 2000.
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    • For excellent reviews, see: (a) Fuji, K. Chem. Rev. 1993, 93, 2037.
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    • For a recent review of rearrangements of epoxy alcohols, see: (a) Magnusson, G. Org. Prep. Proced. Int. 1990, 22, 547. (b) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 733-775.
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For a recent review of rearrangements of epoxy alcohols, see: (a) Magnusson, G. Org. Prep. Proced. Int. 1990, 22, 547. (b) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 733-775.
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    • Ojima, I., Ed.; VCH: Weinheim, Germany; Chapter 4.2
    • (b) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, Germany, 1993; Chapter 4.2.
    • (1993) Catalytic Asymmetric Synthesis
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    • For recent synthetic applications of the Jacobsen and Shi epoxidations in the synthesis of structurally complex natural products, see: (a) Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 2000, 122, 9328. (b) Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2002, 124, 8188. (c) McDonald, F. E.; Bravo, F.; Wang, X.; Wei, X.; Toganoh, M.; Rodríguez, J. R.; Do, B.; Neiwert, W. A.; Hardcastle, K. I. J. Org. Chem. 2002, 67, 2515.
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    • Xiong, Z.1    Corey, E.J.2
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    • For recent synthetic applications of the Jacobsen and Shi epoxidations in the synthesis of structurally complex natural products, see: (a) Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 2000, 122, 9328. (b) Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2002, 124, 8188. (c) McDonald, F. E.; Bravo, F.; Wang, X.; Wei, X.; Toganoh, M.; Rodríguez, J. R.; Do, B.; Neiwert, W. A.; Hardcastle, K. I. J. Org. Chem. 2002, 67, 2515.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8188
    • Burova, S.A.1    McDonald, F.E.2
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    • For recent synthetic applications of the Jacobsen and Shi epoxidations in the synthesis of structurally complex natural products, see: (a) Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 2000, 122, 9328. (b) Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2002, 124, 8188. (c) McDonald, F. E.; Bravo, F.; Wang, X.; Wei, X.; Toganoh, M.; Rodríguez, J. R.; Do, B.; Neiwert, W. A.; Hardcastle, K. I. J. Org. Chem. 2002, 67, 2515.
    • (2002) J. Org. Chem. , vol.67 , pp. 2515
    • McDonald, F.E.1    Bravo, F.2    Wang, X.3    Wei, X.4    Toganoh, M.5    Rodríguez, J.R.6    Do, B.7    Neiwert, W.A.8    Hardcastle, K.I.9
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    • note
    • 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.
  • 83
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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.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11633
    • Saito, T.1    Suzuki, T.2    Morimoto, M.3    Akiyama, C.4    Ochiai, T.5    Takeuchi, K.6    Matsumoto, T.7    Suzuki, K.8
  • 84
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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.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4765
    • Li, J.1    Jeong, S.2    Esser, L.3    Harran, P.G.4


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