SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

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

Total synthesis of (+)-asteltoxin

(4) Eom, Khee Dong a Raman, J Venkat a Kim, Heejin a Cha, Jin Kun a,b

a UNIVERSITY OF ALABAMA (United States)

b WAYNE STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; OLEFINS; STEREOCHEMISTRY;

OLEFINATION;

BIOSYNTHESIS;

2 PYRONE DERIVATIVE; ALDEHYDE; ASTELTOXIN; EPOXIDE; LEWIS ACID; MYCOTOXIN; PHOSPHONIC ACID DERIVATIVE; SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PINACOL REARRANGEMENT; STEREOCHEMISTRY;

ASPERGILLUS; MYCOTOXINS; PYRONES; STEREOISOMERISM;

EID: 0038292969 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja034332q Document Type: Article

Times cited : (41)

References (84)

1
- 37049104145
- (a) Kruger, G. J.; Steyn, P. S.; Vleggaar, R.; Rabie, C. J. J. Chem. Soc., Chem. Commun. 1979, 441.
- (1979) J. Chem. Soc., Chem. Commun. , pp. 441
- Kruger, G.J.¹ Steyn, P.S.² Vleggaar, R.³ Rabie, C.J.⁴

2
- 0021237449
- (b) Steyn, P. S.; Vleggarr, R. J. Chem. Soc., Chem. Commun. 1984, 977.
- (1984) J. Chem. Soc., Chem. Commun. , pp. 977
- Steyn, P.S.¹ Vleggarr, R.²

3
- 37049103201
- (c) de Jesus, A. E.; Steyn, P. S.; Vleggarr, R. J. Chem. Soc., Chem. Commun. 1985, 1633.
- (1985) J. Chem. Soc., Chem. Commun. , pp. 1633
- De Jesus, A.E.¹ Steyn, P.S.² Vleggarr, R.³

4
- 84942072527
- (d) Vleggaar, R. Pure Appl. Chem. 1986, 58, 239.
- (1986) Pure Appl. Chem. , vol.58 , pp. 239
- Vleggaar, R.¹

5
- 0001707503
- (a) Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1983, 105, 6723.
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 6723
- Schreiber, S.L.¹ Satake, K.²

6
- 0021225970
- (b) Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1984, 106, 4186.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 4186
- Schreiber, S.L.¹ Satake, K.²

7
- 0022527624
- (c) Schreiber, S. L.; Satake, K. Tetrahedron Lett. 1986, 27, 2575.
- (1986) Tetrahedron Lett. , vol.27 , pp. 2575
- Schreiber, S.L.¹ Satake, K.²

8
- 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.
- (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
- 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
- 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

18
- 0018371450
- (a) Linnett, P. E.; Beechey, R. B. Methods Enzymol. 1979, 55, 472.
- (1979) Methods Enzymol. , vol.55 , pp. 472
- Linnett, P.E.¹ Beechey, R.B.²

19
- 0019775194
- (b) Satre, M. Biochem. Biophys. Res. Commun. 1981, 100, 267.
- (1981) Biochem. Biophys. Res. Commun. , vol.100 , pp. 267
- Satre, M.¹

20
- 0009689584
- (a) Sankawa, U.; Shimada, H.; Kobayashi, T.; Ebizuka, Y.; Yamamoto, Y.; Noguchi, H.; Seto, H. Heterocycles 1982, 19, 1053.
- (1982) Heterocycles , vol.19 , pp. 1053
- Sankawa, U.¹ Shimada, H.² Kobayashi, T.³ Ebizuka, Y.⁴ Yamamoto, Y.⁵ Noguchi, H.⁶ Seto, H.⁷

21
- 0021922068
- (b) Townsend, C. A.; Christensen, S. B. J. Am. Chem. Soc. 1985, 107, 270.
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 270
- Townsend, C.A.¹ Christensen, S.B.²

22
- 0001038483
- For an excellent review on the biosynthesis of aflatoxins, see: (c) Minto, R. E.; Townsend, C. A. Chem. Rev. 1997, 97, 2537.
- (1997) Chem. Rev. , vol.97 , pp. 2537
- Minto, R.E.¹ Townsend, C.A.²

23
- 0038136449
- 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.
- (1985) J. Org. Chem. , vol.50 , pp. 5428
- Townsend, C.A.¹ Davis, S.G.² Koreeda, M.³ Hulin, B.⁴

24
- 0024554041
- 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.
- (1989) Tetrahedron , vol.45 , pp. 2263
- Townsend, C.A.¹ Isomura, Y.² Davis, S.G.³ Hodge, J.A.⁴

25
- 0023851960
- (a) Tadano, K.-i.; Yamada, H.; Idogaki, Y.; Ogawa, S.; Suami, T. Tetrahedron Lett. 1988, 29, 655.
- (1988) Tetrahedron Lett. , vol.29 , pp. 655
- Tadano, K.-I.¹ Yamada, H.² Idogaki, Y.³ Ogawa, S.⁴ Suami, T.⁵

26
- 0009143937
- (b) Tadano, K.-i.; Yamada, H.; Idogaki, Y.; Ogawa, S.; Suami, T. Tetrahedron 1990, 46, 2353.
- (1990) Tetrahedron , vol.46 , pp. 2353
- Tadano, K.-I.¹ Yamada, H.² Idogaki, Y.³ Ogawa, S.⁴ Suami, T.⁵

27
- 0025071568
- Nishiyama, S.; Kanai, H.; Yamamura, S. Bull. Chem. Soc. Jpn. 1990, 63, 1322.
- (1990) Bull. Chem. Soc. Jpn. , vol.63 , pp. 1322
- Nishiyama, S.¹ Kanai, H.² Yamamura, S.³

28
- 0000847999
- Mulzer, J.; Mohr, J.-T. J. Org. Chem. 1994, 59, 1160.
- (1994) J. Org. Chem. , vol.59 , pp. 1160
- Mulzer, J.¹ Mohr, J.-T.²

29
- 0028945712
- (a) Raman, J. V.; Lee, H. K.; Vleggaar, R.; Cha, J. K. Tetrahedron Lett. 1995, 36, 3095.
- (1995) Tetrahedron Lett. , vol.36 , pp. 3095
- Raman, J.V.¹ Lee, H.K.² Vleggaar, R.³ Cha, J.K.⁴

30
- 0038813194
- Ph.D. Dissertation, The University of Alabama
- Taken in part from the following: (b) Kim, H. Ph.D. Dissertation, The University of Alabama, 1997.
- (1997)
- Kim, H.¹

31
- 0038475406
- Ph.D. Dissertation, The University of Alabama, December
- (c) Eom, K. D. Ph.D. Dissertation, The University of Alabama, December 2000.
- (2000)
- Eom, K.D.¹

32
- 0001521888
- For excellent reviews, see: (a) Fuji, K. Chem. Rev. 1993, 93, 2037.
- (1993) Chem. Rev. , vol.93 , pp. 2037
- Fuji, K.¹

33
- 0032473509
- (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388
- Corey, E.J.¹ Guzman-Perez, A.²

34
- 0035905575
- (c) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4591
- Christoffers, J.¹ Mann, A.²

35
- 0000449913
- (d) Martin, S. F. Tetrahedron 1980, 36, 419.
- (1980) Tetrahedron , vol.36 , pp. 419
- Martin, S.F.¹

36
- 0000648050
- (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-i. J. Am. Chem. Soc. 1986, 108, 3827.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 3827
- Maruoka, K.¹ Hasegawa, M.² Yamamoto, H.³ Suzuki, K.⁴ Shimazaki, M.⁵ Tsuchihashi, G.-I.⁶

37
- 0038813191
- (b) Suzuki, K.; Shimazaki, M.; Tsuchihashi, G.-i. Tetrahedron Lett. 1986, 27, 6237.
- (1986) Tetrahedron Lett. , vol.27 , pp. 6237
- Suzuki, K.¹ Shimazaki, M.² Tsuchihashi, G.-I.³

38
- 0008509207
- (c) Suzuki, K.; Matsumoto, T.; Tomooka, K.; Matsumoto, K.; Tsuchihashi, G.-i. Chem. Lett. 1987, 113.
- (1987) Chem. Lett. , pp. 113
- Suzuki, K.¹ Matsumoto, T.² Tomooka, K.³ Matsumoto, K.⁴ Tsuchihashi, G.-I.⁵

39
- 0000759205
- (d) Suzuki, K.; Miyazawa, M.; Tsuchihashi, G.-i. Tetrahedron Lett. 1987, 28, 3515.
- (1987) Tetrahedron Lett. , vol.28 , pp. 3515
- Suzuki, K.¹ Miyazawa, M.² Tsuchihashi, G.-I.³

40
- 0000957327
- (e) Shimazaki, M.; Hara, H.; Suzuki, K.; Tsuchihashi, G.-i. Tetrahedron Lett. 1987, 28, 5891.
- (1987) Tetrahedron Lett. , vol.28 , pp. 5891
- Shimazaki, M.¹ Hara, H.² Suzuki, K.³ Tsuchihashi, G.-I.⁴

41
- 0023899187
- (f) Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G.-i. Tetrahedron 1988, 44, 4061.
- (1988) Tetrahedron , vol.44 , pp. 4061
- Suzuki, K.¹ Miyazawa, M.² Shimazaki, M.³ Tsuchihashi, G.-I.⁴

42
- 0037798697
- (g) Suzuki, K. J. Synth. Org. Chem. Jpn. 1988, 46, 49.
- (1988) J. Synth. Org. Chem. Jpn. , vol.46 , pp. 49
- Suzuki, K.¹

43
- 0038136446
- (h) Shimazaki, M.; Hara, H.; Suzuki, K. Tetrahedron Lett. 1989, 30, 5443.
- (1989) Tetrahedron Lett. , vol.30 , pp. 5443
- Shimazaki, M.¹ Hara, H.² Suzuki, K.³

44
- 0025299418
- (i) Shimazaki, M.; Morimoto, M.; Suzuki, K. Tetrahedron Lett. 1990, 31, 3335.
- (1990) Tetrahedron Lett. , vol.31 , pp. 3335
- Shimazaki, M.¹ Morimoto, M.² Suzuki, K.³

45
- 0029814942
- (j) Nagasawa, T.; Taya, K.; Kitamura, M.; Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949. Cf.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 8949
- Nagasawa, T.¹ Taya, K.² Kitamura, M.³ Suzuki, K.⁴

46
- 0001285095
- (k) Cheer, C. J.; Johnson, C. R. J. Am. Chem. Soc. 1968, 90, 178.
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 178
- Cheer, C.J.¹ Johnson, C.R.²

47
- 0001076746
- (a) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 6431
- Maruoka, K.¹ Ooi, T.² Yamamoto, H.³

48
- 0000526471
- (b) Maruoka, K.; Nagahara, S.; Ooi, T.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 5607.
- (1989) Tetrahedron Lett. , vol.30 , pp. 5607
- Maruoka, K.¹ Nagahara, S.² Ooi, T.³ Yamamoto, H.⁴

49
- 0009143850
- (c) Maruoka, K.; Bureau, R.; Yamamoto, H. Synlett 1991, 363.
- (1991) Synlett , pp. 363
- Maruoka, K.¹ Bureau, R.² Yamamoto, H.³

50
- 0025768606
- (d) Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983.
- (1991) Tetrahedron , vol.47 , pp. 6983
- Maruoka, K.¹ Ooi, T.² Nagahara, S.³ Yamamoto, H.⁴

51
- 0000079239
- (e) Maruoka, K.; Sato, J.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5449.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5449
- Maruoka, K.¹ Sato, J.² Yamamoto, H.³

52
- 0026549836
- (f) Maruoka, K.; Ooi, T.; Yamamoto, H. Tetrahedron 1992, 48, 3303.
- (1992) Tetrahedron , vol.48 , pp. 3303
- Maruoka, K.¹ Ooi, T.² Yamamoto, H.³

53
- 0026534429
- (g) Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749.
- (1992) Tetrahedron , vol.48 , pp. 3749
- Maruoka, K.¹ Sato, J.² Yamamoto, H.³

54
- 0008251547
- (h) Ooi, K.; Maruoka, K.; Yamamoto, H. Org. Synth. 1995, 72, 95.
- (1995) Org. Synth. , vol.72 , pp. 95
- Ooi, K.¹ Maruoka, K.² Yamamoto, H.³

55
- 0000787875
- See also: (i) Nemoto, H.; Ishibashi, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1992, 57, 1707.
- (1992) J. Org. Chem. , vol.57 , pp. 1707
- Nemoto, H.¹ Ishibashi, H.² Nagamochi, M.³ Fukumoto, K.⁴

56
- 0028327029
- (j) Nemoto, H.; Nagamochi, M.; Ishibashi, H.; Fukumoto, K. J. Org. Chem. 1994, 59, 74.
- (1994) J. Org. Chem. , vol.59 , pp. 74
- Nemoto, H.¹ Nagamochi, M.² Ishibashi, H.³ Fukumoto, K.⁴

57
- 0004564599
- Morrison, J. D., Ed.; Academic Press: Orlando, FL, Chapter 8
- Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis - Chiral Catalysis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1985; Vol. 5, Chapter 8.
- (1985) Asymmetric Synthesis - Chiral Catalysis , vol.5
- Finn, M.G.¹ Sharpless, K.B.²

58
- 0000362240
- 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.
- (1990) Org. Prep. Proced. Int. , vol.22 , pp. 547
- Magnusson, G.¹

59
- 0001312924
- 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.
- (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733-775
- Rickborn, B.¹

60
- 0001092579
- (a) Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson, A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944.
- (1993) J. Org. Chem. , vol.58 , pp. 5944
- Marson, C.M.¹ Walker, A.J.² Pickering, J.³ Hobson, A.D.⁴ Wrigglesworth, R.⁵ Edge, S.J.⁶

61
- 0027366321
- (b) Marson, C. M.; Harper, S.; Walker, A. J.; Pickering, J.; Campbell, J.; Wrigglesworth, R.; Edge, S. J. Tetrahedron 1993, 49, 10339.
- (1993) Tetrahedron , vol.49 , pp. 10339
- Marson, C.M.¹ Harper, S.² Walker, A.J.³ Pickering, J.⁴ Campbell, J.⁵ Wrigglesworth, R.⁶ Edge, S.J.⁷

62
- 0001647186
- (a) Tu, Y. Q.; Sun, L. D.; Wang, P. Z. J. Org. Chem. 1999, 64, 629.
- (1999) J. Org. Chem. , vol.64 , pp. 629
- Tu, Y.Q.¹ Sun, L.D.² Wang, P.Z.³

63
- 0035887126
- (b) Fan, C.-A.; Wang, B.-M.; Tu, Y.-Q.; Song, Z.-L. Angew. Chem., Int. Ed. 2001, 40, 3877.
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3877
- Fan, C.-A.¹ Wang, B.-M.² Tu, Y.-Q.³ Song, Z.-L.⁴

64
- 0029130040
- (a) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 7379
- Jung, M.E.¹ D'Amico, D.C.²

65
- 0034658918
- (b) Jung, M. E.; Marquez, R. Org. Lett. 2000, 2, 1669.
- (2000) Org. Lett. , vol.2 , pp. 1669
- Jung, M.E.¹ Marquez, R.²

66
- 8544276578
- See also: (c) Kita, Y.; Kitagaki, S.; Yoshida, Y.; Mihara, S.; Fang, D.-F.; Kondo, M.; Okamoto, S.; Imai, R.; Akai, S.; Fujioka, H. J. Org. Chem. 1997, 62, 4991.
- (1997) J. Org. Chem. , vol.62 , pp. 4991
- Kita, Y.¹ Kitagaki, S.² Yoshida, Y.³ Mihara, S.⁴ Fang, D.-F.⁵ Kondo, M.⁶ Okamoto, S.⁷ Imai, R.⁸ Akai, S.⁹ Fujioka, H.¹⁰

67
- 9344259269
- (a) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4415
- Allain, E.J.¹ Hager, L.P.² Deng, L.³ Jacobsen, E.N.⁴

68
- 0038136442
- 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
- Jacobsen, E.N.¹

69
- 0033526360
- (c) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4147
- Annis, D.A.¹ Jacobsen, E.N.²

70
- 0030665236
- Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 11224
- Wang, Z.-X.¹ Tu, Y.² Frohn, M.³ Zhang, J.-R.⁴ Shi, Y.⁵

71
- 0034721450
- 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.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9328
- Xiong, Z.¹ Corey, E.J.²

72
- 0037125495
- 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

73
- 0037134176
- 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

74
- 0003536850
- Pergamon: Oxford
- Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, 1983.
- (1983) Stereoelectronic Effects in Organic Chemistry
- Deslongchamps, P.¹

75
- 37049109821
- Cf. (a) Lythgoe, B.; Moran, T. A.; Nambudiry, M. E. N.; Ruston, S. J. Chem. Soc., Perkin Trans. 1 1976, 2386.
- (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 2386
- Lythgoe, B.¹ Moran, T.A.² Nambudiry, M.E.N.³ Ruston, S.⁴

76
- 0030993705
- (b) Mouné, S.; Niel, G.; Busquet, M.; Eggleston, I.; Jouin, P. J. Org. Chem. 1997, 62, 3332.
- (1997) J. Org. Chem. , vol.62 , pp. 3332
- Mouné, S.¹ Niel, G.² Busquet, M.³ Eggleston, I.⁴ Jouin, P.⁵

77
- 0007464330
- Cooke, M. P. Jr. J. Org. Chem. 1982, 47, 4963.
- (1982) J. Org. Chem. , vol.47 , pp. 4963
- Cooke M.P., Jr.¹

78
- 0031950990
- Kim, H.; Lee, S.-K.; Lee, D.; Cha, J. K. Synth. Commun. 1998, 28, 729.
- (1998) Synth. Commun. , vol.28 , pp. 729
- Kim, H.¹ Lee, S.-K.² Lee, D.³ Cha, J.K.⁴

79
- 33748542524
- (a) Johnson, F. Chem. Rev. 1968, 68, 375.
- (1968) Chem. Rev. , vol.68 , pp. 375
- Johnson, F.¹

80
- 33645897192
- (b) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
- (1989) Chem. Rev. , vol.89 , pp. 1841
- Hoffmann, R.W.¹

81
- 4444276636
- Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
- (1994) Chem. Rev. , vol.94 , pp. 2483
- Kolb, H.C.¹ VanNieuwenhze, M.S.² Sharpless, K.B.³

82
- 0038813187
- 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
- 0032544954
- 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
- 0035905352
- 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

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.