SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5883-5889

A Highly Efficient Pinacol Coupling Approach to Trehazolamine Starting from D-Glucose

(4) De Gracia, Isabel Storch a Dietrich, Hansjörg a Bobo, Sofía a Chiara, Jose Luis a

a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001081743 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo980831b Document Type: Article

Times cited : (63)

References (77)

1
- 0000217764
- (a) Clegg, J. S.; Evans, D. R. J. Exp. BM. 1961, 38, 771.
- (1961) J. Exp. BM. , vol.38 , pp. 771
- Clegg, J.S.¹ Evans, D.R.²

2
- 0001693912
- (b) Sacktor, B. S.; Wormser-Shavit, E. J. Biol Chem. 1966, 241, 634.
- (1966) J. Biol Chem. , vol.241 , pp. 634
- Sacktor, B.S.¹ Wormser-Shavit, E.²

3
- 0015879594
- (a) Hecker, L. I.; Sussman, A. S. J. Bacterial. 1973, 115, 592.
- (1973) J. Bacterial. , vol.115 , pp. 592
- Hecker, L.I.¹ Sussman, A.S.²

4
- 0019472791
- (b) Inoue, I.; Shimoda, C. Mol. Gen. Gent. 1981, 183, 32.
- (1981) Mol. Gen. Gent. , vol.183 , pp. 32
- Inoue, I.¹ Shimoda, C.²

5
- 0542428800
- (c) Thevelein, J. M.; den-Hollander, J. A.; Shulman, R. G. Proc. Natl. Acad. Sci. 1982, 79, 3503.
- (1982) Proc. Natl. Acad. Sci. , vol.79 , pp. 3503
- Thevelein, J.M.¹ Den-Hollander, J.A.² Shulman, R.G.³

6
- 0021105443
- (d) Thevelein, J. M.; Jones, K. A. Eur. J. Biochem. 1983, 136, 583.
- (1983) Eur. J. Biochem. , vol.136 , pp. 583
- Thevelein, J.M.¹ Jones, K.A.²

7
- 0014305619
- Sacktor, B. Proc. Natl. Acad. Sci. 1968, 60, 1007.
- (1968) Proc. Natl. Acad. Sci. , vol.60 , pp. 1007
- Sacktor, B.¹

8
- 0026069785
- (a) Ando, O.; Satake, H.; Itoi, K.; Sato, A.; Nakajima, M.; Takahashi, S.; Haruyama, H. J. Antibiot. 1991, 44, 1165.
- (1991) J. Antibiot. , vol.44 , pp. 1165
- Ando, O.¹ Satake, H.² Itoi, K.³ Sato, A.⁴ Nakajima, M.⁵ Takahashi, S.⁶ Haruyama, H.⁷

9
- 0027217993
- (b) Ando, O.; Nakajima, M.; Hamano, K.; Itoi, K.; Takahashi, S.; Takamatsu, Y.; Sato, A.; Enokita, R.; Haruyama, H.; Kinoshita, T. J. Antibiot. 1993, 46, 1116.
- (1993) J. Antibiot. , vol.46 , pp. 1116
- Ando, O.¹ Nakajima, M.² Hamano, K.³ Itoi, K.⁴ Takahashi, S.⁵ Takamatsu, Y.⁶ Sato, A.⁷ Enokita, R.⁸ Haruyama, H.⁹ Kinoshita, T.¹⁰

10
- 0025739081
- Nakayama, T.; Amachi, T.; Murao, S.; Sakai, T.; Shin, T.; Kenny, P. T. M.; Iwashita, T.; Zagorski, M.; Komura, H.; Nomoto, K. J. Chem. Soc., Chem. Commun. 1991, 919. Initially, the structure of the inhibitor isolated from this broth was wrongly assigned as 5-epi-trehazolin, named trehalostatin.
- (1991) J. Chem. Soc., Chem. Commun. , pp. 919
- Nakayama, T.¹ Amachi, T.² Murao, S.³ Sakai, T.⁴ Shin, T.⁵ Kenny, P.T.M.⁶ Iwashita, T.⁷ Zagorski, M.⁸ Komura, H.⁹ Nomoto, K.¹⁰

11
- 0026717048
- (a) Ogawa, S.; Ushida, C.; Yuming, Y. J. Chem. Soc., Chem. Commun. 1992, 886.
- (1992) J. Chem. Soc., Chem. Commun. , pp. 886
- Ogawa, S.¹ Ushida, C.² Yuming, Y.³

12
- 37049089564
- (b) Ogawa, S.; Ushida, C. J. Chem. Soc., Perkin Trans. 1 1992, 1939.
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 1939
- Ogawa, S.¹ Ushida, C.²

13
- 0001286750
- (c) Ogawa, S.; Uchida, C. Chem. Lett. 1993, 173.
- (1993) Chem. Lett. , pp. 173
- Ogawa, S.¹ Uchida, C.²

14
- 37049084260
- (d) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 589.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 589
- Uchida, C.¹ Yamagishi, T.² Ogawa, S.³

15
- 0027082531
- (a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Am. Chem. Soc. 1992, 114, 10065.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 10065
- Kobayashi, Y.¹ Miyazaki, H.² Shiozaki, M.³

16
- 0027403829
- (b) Kobayashi, Y.; Miyazaki, Shiozaki, M. Tetrahedron Lett. 1993, 34, 1505.
- (1993) Tetrahedron Lett. , vol.34 , pp. 1505
- Kobayashi, Y.¹ Miyazaki Shiozaki, M.²

17
- 0028351052
- (c) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813.
- (1994) J. Org. Chem. , vol.59 , pp. 813
- Kobayashi, Y.¹ Miyazaki, H.² Shiozaki, M.³

18
- 0028128999
- Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7461
- Knapp, S.¹ Purandare, A.² Rupitz, K.³ Withers, S.G.⁴

19
- 0028788913
- Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 11811
- Ledford, B.E.¹ Carreira, E.M.²

20
- 37049073483
- (a) Uchida, C.; Kitahashi, H.; Yamagishi, T.; Iwaisaki, Y.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 2775.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2775
- Uchida, C.¹ Kitahashi, H.² Yamagishi, T.³ Iwaisaki, Y.⁴ Ogawa, S.⁵

21
- 0028281645
- (b) Kobayashi, Y.; Shiozaki, M. J. Antibiot. 1994, 47, 243.
- (1994) J. Antibiot. , vol.47 , pp. 243
- Kobayashi, Y.¹ Shiozaki, M.²

22
- 37049081440
- (c) Uchida, C.; Kitahashi, H.; Watanabe, S.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1995, 1707.
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1707
- Uchida, C.¹ Kitahashi, H.² Watanabe, S.³ Ogawa, S.⁴

23
- 0029589855
- (d) Uchida, C.; Yamagishi, T.; Kitahashi, H.; Iwaisaki, Y.; Ogawa, S. Biiorg. Med. Chem. 1995, 3, 1605.
- (1995) Biiorg. Med. Chem. , vol.3 , pp. 1605
- Uchida, C.¹ Yamagishi, T.² Kitahashi, H.³ Iwaisaki, Y.⁴ Ogawa, S.⁵

24
- 0029000476
- (e) Kobayashi, Y.; Shiozaki, M.; Ando, O. J. Org. Chem. 1995, 60, 2570.
- (1995) J. Org. Chem. , vol.60 , pp. 2570
- Kobayashi, Y.¹ Shiozaki, M.² Ando, O.³

25
- 0032473811
- (f) Shiozaki, M.; Ubukata, O.; Haruyama, H.; Yoshiike, R. Tetrahedron Lett. 1998, 39, 1925.
- (1998) Tetrahedron Lett. , vol.39 , pp. 1925
- Shiozaki, M.¹ Ubukata, O.² Haruyama, H.³ Yoshiike, R.⁴

26
- 0344103828
- (a) Uchida, C.; Yamagishi, T.; Ogawa, S. Chem. Lett. 1993, 971.
- (1993) Chem. Lett. , pp. 971
- Uchida, C.¹ Yamagishi, T.² Ogawa, S.³

27
- 0027380562
- (b) Elliot, R. P.; Hui, A.; Fairbanks, A. J.; Nash, R. J.; Winchester, B. G.; Way, G.; Smith, C.; Lamont, R. B.; Storer, R.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 7949.
- (1993) Tetrahedron Lett. , vol.34 , pp. 7949
- Elliot, R.P.¹ Hui, A.² Fairbanks, A.J.³ Nash, R.J.⁴ Winchester, B.G.⁵ Way, G.⁶ Smith, C.⁷ Lamont, R.B.⁸ Storer, R.⁹ Fleet, G.W.J.¹⁰

28
- 37049073483
- (c) Uchida, C.; Kitahashi, H.; Yamagishi, T.; Iwaisaki, Y.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 2775.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2775
- Uchida, C.¹ Kitahashi, H.² Yamagishi, T.³ Iwaisaki, Y.⁴ Ogawa, S.⁵

29
- 0344103826
- (d) Uchida, C.; Ogawa, S. Carbohydr. Lett. 1994, 1, 77.
- (1994) Carbohydr. Lett. , vol.1 , pp. 77
- Uchida, C.¹ Ogawa, S.²

30
- 0028279980
- (e) Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887.
- (1994) Tetrahedron Lett. , vol.35 , pp. 887
- Shiozaki, M.¹ Kobayashi, Y.² Arai, M.³ Haruyama, H.⁴

31
- 0028111228
- (f) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M.; Haruyama, H. J. Antibiot. 1994, 47, 932.
- (1994) J. Antibiot. , vol.47 , pp. 932
- Kobayashi, Y.¹ Miyazaki, H.² Shiozaki, M.³ Haruyama, H.⁴

32
- 0027933794
- (g) Shiozaki, M.; Arai, M.; Kobayashi, Y.; Kasuya, A.; Miyamoto, S.; Furukawa, Y.; Takayama, T.; Haruyama, H. J. Org. Chem. 1994, 59, 4450.
- (1994) J. Org. Chem. , vol.59 , pp. 4450
- Shiozaki, M.¹ Arai, M.² Kobayashi, Y.³ Kasuya, A.⁴ Miyamoto, S.⁵ Furukawa, Y.⁶ Takayama, T.⁷ Haruyama, H.⁸

33
- 0029589855
- (h) Uchida, C.; Yamagishi, T.; Kitahashi, H.; Iwaisaki, Y.; Ogawa, S. Bioorg. Med. Chem. 1995, 3, 1605.
- (1995) Bioorg. Med. Chem. , vol.3 , pp. 1605
- Uchida, C.¹ Yamagishi, T.² Kitahashi, H.³ Iwaisaki, Y.⁴ Ogawa, S.⁵

34
- 37049081440
- (i) Uchida, C.; Kitahashi, H.; Watanabe, S.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1995, 1707.
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1707
- Uchida, C.¹ Kitahashi, H.² Watanabe, S.³ Ogawa, S.⁴

35
- 0029892076
- (j) Uchida, C.; Ogawa, S. Bioorg. Med. Chem. 1996, 4, 275. See, also: Ogawa, S. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim 1998, Chapter 5.
- (1996) Bioorg. Med. Chem. , vol.4 , pp. 275
- Uchida, C.¹ Ogawa, S.²

36
- 0029892076
- Chapleur, Y., Ed.; Wiley-VCH: Weinheim Chapter 5
- (j) Uchida, C.; Ogawa, S. Bioorg. Med. Chem. 1996, 4, 275. See, also: Ogawa, S. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim 1998, Chapter 5.
- (1998) Carbohydrate Mimics: Concepts and Methods
- Ogawa, S.¹

37
- 85140868678
- Camarasa, M. J.; Fernández-Resa, P.; García-López, M. T.; G. de las Heras, F.; Méndez-Castrillón, P. P.; San Félix, A. Synthesis 1984, 509.
- (1984) Synthesis , pp. 509
- Camarasa, M.J.¹ Fernández-Resa, P.² García-López, M.T.³ De Las Heras, F.G.⁴ Méndez-Castrillón, P.P.⁵ San Félix, A.⁶

38
- 0032524799
- After this paper was submitted for publication, a new synthesis of 3 and (+)-6-epitrehazolin appeared in the literature: Li, J.; Lang, F.; Ganem, B. J. Org. Chem. 1998, 63, 3403. For a related formal synthesis of 3, see: Goering, B. K.; Li, J.; Ganem, B. Tetrahedron Lett. 1995, 36, 8905.
- (1998) J. Org. Chem. , vol.63 , pp. 3403
- Li, J.¹ Lang, F.² Ganem, B.³

39
- 0028841036
- After this paper was submitted for publication, a new synthesis of 3 and (+)-6-epitrehazolin appeared in the literature: Li, J.; Lang, F.; Ganem, B. J. Org. Chem. 1998, 63, 3403. For a related formal synthesis of 3, see: Goering, B. K.; Li, J.; Ganem, B. Tetrahedron Lett. 1995, 36, 8905.
- (1995) Tetrahedron Lett. , vol.36 , pp. 8905
- Goering, B.K.¹ Li, J.² Ganem, B.³

40
- 2142715741
- For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A.; Harris, G. R. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Org. React. 1994, 46. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London 1994.
- (1996) Chem. Rev. , vol.96 , pp. 307
- Molander, G.A.¹ Harris, G.R.²

41
- 2142715741
- For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A.; Harris, G. R. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Org. React. 1994, 46. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London 1994.
- (1994) Org. React. , vol.46
- Molander, G.A.¹

42
- 2142715741
- Academic Press: London
- For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A.; Harris, G. R. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Org. React. 1994, 46. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London 1994.
- (1994) Lanthanides in Organic Synthesis
- Imamoto, T.¹

43
- 12044258371
- For a recent review on the use of carbohydrate templates for the preparation of carbocycles, see: Ferner, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
- (1993) Chem. Rev. , vol.93 , pp. 2779
- Ferner, R.J.¹ Middleton, S.²

44
- 0028882256
- (a) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
- (1995) J. Org. Chem. , vol.60 , pp. 6010
- Chiara, J.L.¹ Marco-Contelles, J.² Khiar, N.³ Gallego, P.⁴ Destabel, C.⁵ Bernabé, M.⁶

45
- 0030780809
- (b) Marco-Contelles, J. L.; Gallego, P.; Rodríguez-Fernández, M.; Khiar, N.; Destabel, C.; Bernabé, M.; Martínez-Grau, A.; Chiara, J. L. J. Org. Chem. 1997, 62, 7397.
- (1997) J. Org. Chem. , vol.62 , pp. 7397
- Marco-Contelles, J.L.¹ Gallego, P.² Rodríguez-Fernández, M.³ Khiar, N.⁴ Destabel, C.⁵ Bernabé, M.⁶ Martínez-Grau, A.⁷ Chiara, J.L.⁸

46
- 0542428825
- Chapleur, Y., Ed.; Wiley-VCH: chapter 7
- A part of this work was presented at the 2nd Euroconference on Carbohydrate Mimics; Lago di Garda; 1996. See: Chiara, J. L. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: 1998; chapter 7.
- (1998) Carbohydrate Mimics: Concepts and Methods
- Chiara, J.L.¹

47
- 0026065219
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1991) Tetrahedron Lett. , vol.32 , pp. 1125
- Chiara, J.L.¹ Cabri, W.² Hanessian, S.³

48
- 0025764794
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1991) Tetrahedron Lett. , vol.32 , pp. 5097
- Uenishi, J.¹ Masuda, S.² Wakabayashi, S.³

49
- 0028364675
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1994) Tetrahedron Lett. , vol.35 , pp. 2969
- Chiara, J.L.¹ Martín-Lomas, M.²

50
- 0028106715
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1994) Tetrahedron Lett. , vol.35 , pp. 6671
- Guidot, J.P.¹ Le Gall, T.² Mioskowski, C.³

51
- 0029149758
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1895
- Chiara, J.L.¹ Valle, N.²

52
- 0010620533
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1995) Carbohydr. Lett. , vol.1 , pp. 215
- Perrin, E.¹ Mallet, J.-M.² Sinay, P.³

53
- 0030049755
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1996) Tetrahedron Lett. , vol.37 , pp. 885
- Sawada, T.¹ Shirai, R.² Iwasaki, S.³

54
- 0030817673
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1997) Tetrahedron Lett. , vol.38 , pp. 6497
- Kornienko, A.¹ D'Alarcao, M.²

55
- 0030945610
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1997) J. Org. Chem. , vol.62 , pp. 1916
- Carpintero, M.¹ Fernández-Mayoralas, A.² Jaramillo, C.³

56
- 0030811538
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1997) Tetrahedron , vol.53 , pp. 11767
- Adinolfi, M.¹ Barone, G.² Iadonisi, A.³ Mangoni, L.⁴ Manna, R.⁵

57
- 33748605086
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 41
- Jenkins, D.J.¹ Potter, B.V.L.²

58
- 0032473816
- For examples in the carbohydrate field, see: (a) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125. (b) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097. (c) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969. (d) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 6671. (e) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895. (f) Perrin, E.; Mallet, J.-M.; Sinay, P. Carbohydr. Lett. 1995, 1, 215. (g) Sawada, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 885. (h) Kornienko, A.; d'Alarcao, M. Tetrahedron Lett. 1997, 38, 6497. (i) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L.; Manna, R. Tetrahedron 1997, 53, 11767. (k) Jenkins, D. J.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1 1998, 41. (l) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
- (1998) Tetrahedron Lett. , vol.39 , pp. 2021
- Adinolfi, M.¹ Barone, G.² Iadonisi, A.³ Mangoni, L.⁴

59
- 0001953710
- Decoster, E.; Lacombe, J.-M.; Streber, J.-L.; Ferrari, B.; Pavia, A. A. J. Carbohydr. Chem. 1983, 2, 329.
- (1983) J. Carbohydr. Chem. , vol.2 , pp. 329
- Decoster, E.¹ Lacombe, J.-M.² Streber, J.-L.³ Ferrari, B.⁴ Pavia, A.A.⁵

60
- 33847086035
- Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693
- Girard, P.¹ Namy, J.L.² Kagan, H.B.³

61
- 0032555461
- 181 The slightly different diastereoselectivity obtained in each case is probably a consequence of the different experimental procedures followed.
- (1998) J. Org. Chem. , vol.63 , pp. 5877
- Boiron, A.¹ Zillig, P.² Faber, D.³ Giese, B.⁴

62
- 0542452572
- note
- Two very minor cyclopentanediols (A, 0.33%; B, 0.53% yield) could also be isolated by chromatography and characterized when the reaction was performed on gram scale (see Experimental Section). Neither of these compounds formed an isopropylidene acetal, showing that they are in fact the other two possible diastereoisomeric products, with trans relative stereochemistry at the new stereocenters (see Supporting Information for NOESY data).

63
- 0001764957
- Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8236
- Molander, G.A.¹ Kenny, C.²

64
- 0542428827
- note
- 3 in DMF or toluene at room temperature to 125 °C.

65
- 0542452570
- note
- 2 afforded only starting material.

66
- 0015922297
- (a) Greenberg, S.; Moffatt, J. G. J. Am. Chem. Soc. 1973, 95, 4016.
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 4016
- Greenberg, S.¹ Moffatt, J.G.²

67
- 0000903234
- (b) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367.
- (1984) Tetrahedron Lett. , vol.25 , pp. 367
- Robins, M.J.¹ Hansske, F.² Low, N.H.³ Park, J.I.⁴

68
- 0026495369
- Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515.
- (1992) Tetrahedron , vol.48 , pp. 10515
- Kolb, H.C.¹ Sharpless, K.B.²

69
- 33947483562
- Corey, E. J.; Winter, R. A. E. J. Am. Chem. Soc. 1963, 85, 2677.
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 2677
- Corey, E.J.¹ Winter, R.A.E.²

70
- 0542404913
- 7c for the epoxidation of a closely related cyclopentene derivative
- 7c for the epoxidation of a closely related cyclopentene derivative.

71
- 0012815040
- Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974. For a recent review, see: Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojiraa, I., Ed.; VCH Publishers: New York 1993; pp 103-158.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 5974
- Katsuki, T.¹ Sharpless, K.B.²

72
- 0001373911
- Ojiraa, I., Ed.; VCH Publishers: New York
- Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974. For a recent review, see: Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojiraa, I., Ed.; VCH Publishers: New York 1993; pp 103-158.
- (1993) Catalytic Asymmetric Synthesis , pp. 103-158
- Johnson, R.A.¹ Sharpless, K.B.²

73
- 37049070376
- (a) Angibeaud, P.; Utille, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 1490.
- (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 1490
- Angibeaud, P.¹ Utille, J.-P.²

74
- 0025826188
- (b) Angibeaud, P.; Utille, J.-P. Synthesis 1991, 737.
- (1991) Synthesis , pp. 737
- Angibeaud, P.¹ Utille, J.-P.²

75
- 0030750991
- Ynag, G.; Ding, X.; Kong, F. Tetrahedron Lett. 1997, 38, 6725.
- (1997) Tetrahedron Lett. , vol.38 , pp. 6725
- Ynag, G.¹ Ding, X.² Kong, F.³

76
- 0542452573
- 1H NMR of the crude reaction mixture
- 1H NMR of the crude reaction mixture.

77
- 0000315480
- VanderWerf, C. A.; Heisler, R. Y.; McEwen, W. E. J. Am. Chem. Soc. 1954, 76, 1231.
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 1231
- Vanderwerf, C.A.¹ Heisler, R.Y.² McEwen, W.E.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.