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Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2525-2529

Novel IBX-mediated processes for the synthesis of amino sugars and libraries thereof

(4) Nicolaou, K C a,b Baran, Phil S a,b Zhong, Yong Li a,b Vega, Juan A a,b

a SCRIPPS RESEARCH INSTITUTE (United States)

b UNIVERSITY OF CALIFORNIA (United States)

Author keywords

Amino sugars; Carbohydrates; Iodine reagents; Synthetic methods

Indexed keywords

3 IODOBENZOIC ACID; ALLYL ALCOHOL; AMINOSUGAR; BICYCLO[5.3.1]UNDECANE DERIVATIVE; CERIUM NITRATE; ISOCYANIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034679468 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/1521-3773(20000717)39:14<2525::AID-ANIE2525>3.0.CO;2-1 Document Type: Article

Times cited : (113)

References (74)

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- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. , vol.112 , pp. 1135-1138
- Nicolaou, A.K.C.¹ Snyder, S.² Bigot, A.³ Pfefferkorn, J.⁴

2
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- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
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3
- 0006729952
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. , vol.112 , pp. 1131-1135
- Nicolaou, K.C.¹ Mitchell, H.J.² Fylaktakidou, K.C.³ Suzuki, H.⁴ Rodriguez, R.⁵

4
- 0034678005
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1089-1093

5
- 0000235735
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. , vol.112 , pp. 750-755
- Pfefferkorn, J.A.¹ Cao, G.-Q.²

6
- 0034681474
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 734-739

7
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- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. , vol.112 , pp. 755-759
- Nicolaou, K.C.¹ Pfefferkorn, J.A.² Cao, G.-Q.³

8
- 0034681559
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 739-743

9
- 0001227495
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. , vol.112 , pp. 636-639
- Nicolaou, K.C.¹ Zhong, Y.-L.² Baran, P.S.³

10
- 0034603046
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 622-625

11
- 0001363940
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. , vol.112 , pp. 639-642
- Nicolaou, K.C.¹ Zhong, Y.-L.² Baran, P.S.³

12
- 0034602983
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 625-628

13
- 0032879750
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
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- Tan, D.S.¹ Foley, M.A.² Stockwell, B.R.³ Shair, M.D.⁴ Schreiber, S.L.⁵

14
- 0033579147
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 10648-10649
- Lee, D.¹ Sello, J.K.² Schreiber, S.L.³

15
- 0032569205
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8565-8566
- Tan, D.S.¹ Foley, M.A.² Shair, M.D.³ Schreiber, S.L.⁴

16
- 0039938898
- Wiley, New York
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (1998) Comb. Chem. Mol. Diversity Drug Discovery , pp. 516
- Gordon, E.M.¹ Kerwin, J.F.²

17
- 0032253177
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (1998) Mol. Diversity , vol.3 , pp. 199-233
- Dolle, R.E.¹

18
- 0033156688
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235-282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
- (1999) J. Comb. Chem. , vol.1 , pp. 235-282
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19
- 0029829698
- For some recent examples, see: a) K. C. Nicolaou, S. Snyder, A. Bigot, J. Pfefferkorn, Angew. Chem. 2000, 112, 1135-1138; Angew. Chem. Int. Ed. 2000, 39, 1093-1096; b) K. C. Nicolaou, H. J. Mitchell, K. C. Fylaktakidou, H. Suzuki, R. Rodriguez, Angew. Chem. 2000, 112, 1131-1135; Angew. Chem. Int. Ed. 2000, 39, 1089-1093; c) J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739; d) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 755-759; Angew. Chem. Int. Ed. 2000, 39, 739-743; e) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625; f) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628; g) D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087; h) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649; i) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1998, 120, 8565-8566; for reviews of molecular diversity, see: j) Comb. Chem. Mol. Diversity Drug Discovery (Eds.: E. M. Gordon, J. F. Kerwin, Jr.), Wiley, New York, 1998, p. 516; R. E. Dolle, Mol. Diversity 1998, 3, 199-233; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235- 282; H. Fenniri, Curr. Med. Chem. 1996, 3, 343-378.
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36
- 0028845943
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37
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38
- 85021167319
- note
- Although, with such a mode of reaction as that shown in Scheme 1, one might expect cis delivery to the olefin, trans addition is also conceivable in certain cases. In the absence of a definitive mechanistic trend for this IBX-mediated reaction at the outset of this work, it was left to empirical observation to provide the answer as to the stereochemical outcome.

39
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- [26]

40
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43
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- Compounds 9 and 10 were derived from methyl-α-D-mannose pyranoside and methyl-β-D-galactose pyranoside, unpublished results.

44
- 85021167331
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- Compounds 11 and 12 were derived from l-arabinose, unpublished results.

45
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48
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49
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- Prepared in two steps from ethyl l-lactate by TBS protection (TBSCl, imidazole) and DIBAL reduction (toluene, -78 C).

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58
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59
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- Extensive mechanistic studies dealing with the interactions of periodinanes with anilides will be reported in due course
- Extensive mechanistic studies dealing with the interactions of periodinanes with anilides will be reported in due course.

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- note
- Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Cristallographic Data Centre as supplementary publication no. CCDC-142005. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033: e-mail: deposit@ccdc.cam.ac.uk).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.