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Journal of the American Chemical Society

Volumn 122, Issue 13, 2000, Pages 2995-3000

A novel and practical synthesis of L-hexoses from D-glycono-1,5-lactones

(4) Takahashi, Hideyo a Hitomi, Yuko a Iwai, Yoshinori a Ikegami, Shiro a

a TEIKYO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCONIC ACID; HEXOSE; LACTONE DERIVATIVE; OXAMIC ACID; OXIME DERIVATIVE; SUGAR;

ALKYLATION; AMINATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 0034607294 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja992808t Document Type: Article

Times cited : (62)

References (52)

1
- 0013945168
- (a) Umezawa, H.; Maeda, K.; Takeuchi, T.; Okami, Y. J. Antibiot., Ser. A 1966, 19, 200-209.
- (1966) J. Antibiot., Ser. A , vol.19 , pp. 200-209
- Umezawa, H.¹ Maeda, K.² Takeuchi, T.³ Okami, Y.⁴

2
- 0001856153
- Sigel, H., Ed.; Marcel Dekker: New York
- (b) Sugiura, Y.; Takita, T.; Umezawa, H. In Metal Ions in Biological Systems; Sigel, H., Ed.; Marcel Dekker: New York, 1985; pp 81-108.
- (1985) Metal Ions in Biological Systems , pp. 81-108
- Sugiura, Y.¹ Takita, T.² Umezawa, H.³

3
- 0002234264
- Lukacs, G., Ohno, M., Eds.; Springer-Verlag: New York
- (c) Ohno, M.; Otsuka, M. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: New York, 1990; pp 387-414.
- (1990) Recent Progress in the Chemical Synthesis of Antibiotics , pp. 387-414
- Ohno, M.¹ Otsuka, M.²

4
- 0018134204
- (d) Takita, T.; Muraoka, Y.; Nakatani, T.; Fujii, A.; Umezawa, Y.; Naganawa, H.; Umezawa, H. J. Antibiot. 1978, 31, 801-804.
- (1978) J. Antibiot. , vol.31 , pp. 801-804
- Takita, T.¹ Muraoka, Y.² Nakatani, T.³ Fujii, A.⁴ Umezawa, Y.⁵ Naganawa, H.⁶ Umezawa, H.⁷

5
- 0020416103
- (e) Aoyagi, Y.; Katano, K.; Suguna, H.; Pimeau, J.; Chang, L.-H.; Hecht, S. M. J. Am. Chem. Soc. 1982, 104, 5537-5538.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 5537-5538
- Aoyagi, Y.¹ Katano, K.² Suguna, H.³ Pimeau, J.⁴ Chang, L.-H.⁵ Hecht, S.M.⁶

6
- 0028109186
- (f) Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647-5656.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 5647-5656
- Boger, D.L.¹ Honda, T.²

7
- 0032538002
- (g) Boger, D. L.; Ramsey, T. M.; Cai, H.; Hoehn, S. T.; Stubbe, J. J. Am. Chem. Soc. 1998, 120, 9139-9148.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 9139-9148
- Boger, D.L.¹ Ramsey, T.M.² Cai, H.³ Hoehn, S.T.⁴ Stubbe, J.⁵

8
- 0032508870
- (h) Katano, K.; An, H.; Aoyagi, Y.; Overhand, M.; Sucheck, S. J.; Stevens, W. C., Jr.; Hess, C. D.; Zhou, X.; Hecht, S. M. J. Am. Chem. Soc. 1998, 120, 11285-11296.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11285-11296
- Katano, K.¹ An, H.² Aoyagi, Y.³ Overhand, M.⁴ Sucheck, S.J.⁵ Stevens Jr., W.C.⁶ Hess, C.D.⁷ Zhou, X.⁸ Hecht, S.M.⁹

9
- 0002707929
- (a) Sinay, P.; Jacquinet, J.-C. Carbohydr. Res. 1984, 132, C5-C9.
- (1984) Carbohydr. Res. , vol.132
- Sinay, P.¹ Jacquinet, J.-C.²

10
- 0022970198
- (b) Tollefsen, D. M.; Peacock, M. E.; Monafo, W. J. J. Biol. Chem. 1986, 261, 8854-8858.
- (1986) J. Biol. Chem. , vol.261 , pp. 8854-8858
- Tollefsen, D.M.¹ Peacock, M.E.² Monafo, W.J.³

11
- 0023690338
- (c) Petitou, M.; Lormeau, J.-C.; Choay, J. Eur. J. Biochem. 1988, 176, 637-640.
- (1988) Eur. J. Biochem. , vol.176 , pp. 637-640
- Petitou, M.¹ Lormeau, J.-C.² Choay, J.³

12
- 0025059489
- (d) Maimone, M. M.; Tollefsen, D. M. J. Biol. Chem. 1990, 265, 18263-18271.
- (1990) J. Biol. Chem. , vol.265 , pp. 18263-18271
- Maimone, M.M.¹ Tollefsen, D.M.²

13
- 0030052925
- (a) Iimori, T.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 1996, 37, 649-652.
- (1996) Tetrahedron Lett. , vol.37 , pp. 649-652
- Iimori, T.¹ Takahashi, H.² Ikegami, S.³

14
- 0032541712
- (b) Takahashi, H.; Iimori, T.; Ikegami, S. Tetrahedron Lett. 1998, 39, 6939-6942.
- (1998) Tetrahedron Lett. , vol.39 , pp. 6939-6942
- Takahashi, H.¹ Iimori, T.² Ikegami, S.³

15
- 0032564530
- (c) Takahashi, H.; Kittaka, H.; Ikegami, S. Tetrahedron Lett. 1998, 39, 9703-9706.
- (1998) Tetrahedron Lett. , vol.39 , pp. 9703-9706
- Takahashi, H.¹ Kittaka, H.² Ikegami, S.³

16
- 0032564589
- (d) Takahashi, H.; Kittaka, H.; Ikegami, S. Tetrahedron Lett. 1998, 39, 9707-9710.
- (1998) Tetrahedron Lett. , vol.39 , pp. 9707-9710
- Takahashi, H.¹ Kittaka, H.² Ikegami, S.³

17
- 0018697756
- (a) Mattingly, P. G.; Kerwin, J. F., Jr.; Miller, M. J. J. Am. Chem. Soc. 1979, 101, 3983-3985.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 3983-3985
- Mattingly, P.G.¹ Kerwin Jr., J.F.² Miller, M.J.³

18
- 0021062005
- (b) Morrison, M. A.; Miller, M. J. J. Org. Chem. 1983, 48, 4421-4423.
- (1983) J. Org. Chem. , vol.48 , pp. 4421-4423
- Morrison, M.A.¹ Miller, M.J.²

19
- 0020518168
- (c) Miller, M. J.; Mattingly, P. G. Tetrahedron 1983, 39, 2563-2570.
- (1983) Tetrahedron , vol.39 , pp. 2563-2570
- Miller, M.J.¹ Mattingly, P.G.²

20
- 0025907559
- (d) Farouz, F.; Miller, M. J. Tetrahedron Lett. 1991, 32, 3305-3308.
- (1991) Tetrahedron Lett. , vol.32 , pp. 3305-3308
- Farouz, F.¹ Miller, M.J.²

21
- 0019205018
- For a discussion of O-/N-alkylation selectivity in Mitsunobu reaction of various amides and carbamates, see: (a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026-7032. (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229-1230. (c) Krook, M. A.; Miller, M. J., J. Org. Chem. 1985, 50, 1126-1128. (d) Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810. (e) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267-6270. (f) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655-658.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7026-7032
- Miller, M.J.¹ Mattingly, P.G.² Morrison, M.A.³ Kerwin Jr., J.F.⁴

22
- 0000049690
- For a discussion of O-/N-alkylation selectivity in Mitsunobu reaction of various amides and carbamates, see: (a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026-7032. (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229-1230. (c) Krook, M. A.; Miller, M. J., J. Org. Chem. 1985, 50, 1126-1128. (d) Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810. (e) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267-6270. (f) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655-658.
- (1981) J. Org. Chem. , vol.46 , pp. 1229-1230
- Bose, A.K.¹ Sahu, D.P.² Manhas, M.S.³

23
- 0000145298
- For a discussion of O-/N-alkylation selectivity in Mitsunobu reaction of various amides and carbamates, see: (a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026-7032. (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229-1230. (c) Krook, M. A.; Miller, M. J., J. Org. Chem. 1985, 50, 1126-1128. (d) Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810. (e) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267-6270. (f) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655-658.
- (1985) J. Org. Chem. , vol.50 , pp. 1126-1128
- Krook, M.A.¹ Miller, M.J.²

24
- 0026717117
- For a discussion of O-/N-alkylation selectivity in Mitsunobu reaction of various amides and carbamates, see: (a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026-7032. (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229-1230. (c) Krook, M. A.; Miller, M. J., J. Org. Chem. 1985, 50, 1126-1128. (d) Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810. (e) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267-6270. (f) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655-658.
- (1992) Tetrahedron Lett. , vol.33 , pp. 2807-2810
- Galéotti, N.¹ Montagne, C.² Poncet, J.³ Jouin, P.⁴

25
- 0026788467
- For a discussion of O-/N-alkylation selectivity in Mitsunobu reaction of various amides and carbamates, see: (a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026-7032. (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229-1230. (c) Krook, M. A.; Miller, M. J., J. Org. Chem. 1985, 50, 1126-1128. (d) Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810. (e) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267-6270. (f) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655-658.
- (1992) Tetrahedron Lett. , vol.33 , pp. 6267-6270
- Wipf, P.¹ Miller, C.P.²

26
- 37049082653
- For a discussion of O-/N-alkylation selectivity in Mitsunobu reaction of various amides and carbamates, see: (a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026-7032. (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229-1230. (c) Krook, M. A.; Miller, M. J., J. Org. Chem. 1985, 50, 1126-1128. (d) Galéotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810. (e) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267-6270. (f) Koppel, I.; Koppel, J.; Koppel, I.; Leito, I.; Pihl, V.; Wallin, A.; Grehn, L.; Ragnarsson, U. J. Chem. Soc., Perkin Trans. 2 1993, 655-658.
- (1993) J. Chem. Soc., Perkin Trans. 2 , pp. 655-658
- Koppel, I.¹ Koppel, J.² Koppel, I.³ Leito, I.⁴ Pihl, V.⁵ Wallin, A.⁶ Grehn, L.⁷ Ragnarsson, U.⁸

27
- 85077634689
- Review: Mitsunobu, O. Synthesis 1981, 1-28.
- (1981) Synthesis , pp. 1-28
- Mitsunobu, O.¹

28
- 33845554860
- (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 4976-4978
- Lewis, M.D.¹ Cha, J.K.² Kishi, Y.³

29
- 0030919220
- For the efficient glycosylation utilizing carbohydrate lactone, see: (b) Ohtake, H.; Iimori, T.; Ikegami, S. Tetrahedron Lett. 1997, 38, 3413-3414. (c) Ohtake, H.; Iimori, T.; Ikegami, S. Heterocycles 1998, 47, 685-688. (d) Ohtake, H.; Iimori, T., Ikegami, S. Synlett. 1998, 1420-1422.
- (1997) Tetrahedron Lett. , vol.38 , pp. 3413-3414
- Ohtake, H.¹ Iimori, T.² Ikegami, S.³

30
- 0001105761
- For the efficient glycosylation utilizing carbohydrate lactone, see: (b) Ohtake, H.; Iimori, T.; Ikegami, S. Tetrahedron Lett. 1997, 38, 3413-3414. (c) Ohtake, H.; Iimori, T.; Ikegami, S. Heterocycles 1998, 47, 685-688. (d) Ohtake, H.; Iimori, T., Ikegami, S. Synlett. 1998, 1420-1422.
- (1998) Heterocycles , vol.47 , pp. 685-688
- Ohtake, H.¹ Iimori, T.² Ikegami, S.³

31
- 0003306743
- For the efficient glycosylation utilizing carbohydrate lactone, see: (b) Ohtake, H.; Iimori, T.; Ikegami, S. Tetrahedron Lett. 1997, 38, 3413-3414. (c) Ohtake, H.; Iimori, T.; Ikegami, S. Heterocycles 1998, 47, 685-688. (d) Ohtake, H.; Iimori, T., Ikegami, S. Synlett. 1998, 1420-1422.
- (1998) Synlett. , pp. 1420-1422
- Ohtake, H.¹ Iimori, T.² Ikegami, S.³

32
- 0001771090
- Lewis acid-catalyzed amination of esters: (a) Houghton, R. P.; Williams, C. S. Tetrahedron Lett. 1967, 8, 3929-3931. (b) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993. (c) Lesimple, P.; Bigg, D. C. H. Synthesis 1991, 306-308.
- (1967) Tetrahedron Lett. , vol.8 , pp. 3929-3931
- Houghton, R.P.¹ Williams, C.S.²

33
- 84953502363
- Lewis acid-catalyzed amination of esters: (a) Houghton, R. P.; Williams, C. S. Tetrahedron Lett. 1967, 8, 3929-3931. (b) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993. (c) Lesimple, P.; Bigg, D. C. H. Synthesis 1991, 306-308.
- (1982) Synth. Commun. , vol.12 , pp. 989-993
- Levin, J.I.¹ Turos, E.² Weinreb, S.M.³

34
- 0026013507
- Lewis acid-catalyzed amination of esters: (a) Houghton, R. P.; Williams, C. S. Tetrahedron Lett. 1967, 8, 3929-3931. (b) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993. (c) Lesimple, P.; Bigg, D. C. H. Synthesis 1991, 306-308.
- (1991) Synthesis , pp. 306-308
- Lesimple, P.¹ Bigg, D.C.H.²

35
- 12944294264
- note
- We are now conducting conformational analysis of these anions by employing computer calculations.

36
- 84981749734
- (a) Fisher, E.; Piloty, O. Chem. Ber. 1891, 24, 521-528.
- (1891) Chem. Ber. , vol.24 , pp. 521-528
- Fisher, E.¹ Piloty, O.²

37
- 0001283282
- (b) Evans, M. E.; Parrish, F. W. Carbohydr. Res. 1973, 28, 359-364.
- (1973) Carbohydr. Res. , vol.28 , pp. 359-364
- Evans, M.E.¹ Parrish, F.W.²

38
- 12944268138
- (c) B-Muesser, M.; Defaye, J. Synthesis 1977, 568-569.
- (1977) Synthesis , pp. 568-569
- B-Muesser, M.¹ Defaye, J.²

39
- 0000466033
- (d) B-Muesser, M.; Defaye, J. Methods Carbohydr. Chem. 1980, 8, 177-183.
- (1980) Methods Carbohydr. Chem. , vol.8 , pp. 177-183
- B-Muesser, M.¹ Defaye, J.²

40
- 84985598316
- (e) Köster, R.; Idelmann, P.; Dahlhoff, W. V. Angew. Chem., Int. Ed. Engl. 1980, 19, 547-548.
- (1980) Angew. Chem., Int. Ed. Engl. , vol.19 , pp. 547-548
- Köster, R.¹ Idelmann, P.² Dahlhoff, W.V.³

41
- 0010968123
- (f) Helleur, R.; Rao, V. S.; Perlin, A. S. Carbohydr. Res. 1981, 89, 83-90.
- (1981) Carbohydr. Res. , vol.89 , pp. 83-90
- Helleur, R.¹ Rao, V.S.² Perlin, A.S.³

42
- 0022375105
- (g) Katano, K.; Chang, P.-I.; Millar, A.; Pozsgay, V.; Minster, D. K.; Ohgi, T.; Hecht, S. M. J. Org. Chem, 1985, 50, 5807-5815.
- (1985) J. Org. Chem , vol.50 , pp. 5807-5815
- Katano, K.¹ Chang, P.-I.² Millar, A.³ Pozsgay, V.⁴ Minster, D.K.⁵ Ohgi, T.⁶ Hecht, S.M.⁷

43
- 0025708098
- (h) González, F. S.; Baer, H. H. Carbohydr. Res. 1990, 202, 33-47.
- (1990) Carbohydr. Res. , vol.202 , pp. 33-47
- González, F.S.¹ Baer, H.H.²

44
- 0027967508
- (i) Oshitari, T.; Tomita, M.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 6493-6494.
- (1994) Tetrahedron Lett. , vol.35 , pp. 6493-6494
- Oshitari, T.¹ Tomita, M.² Kobayashi, S.³

45
- 0000373613
- (j) Dondoni, A.; Marra, A.; Massi, A. J. Org. Chem. 1997, 62, 6261-6267.
- (1997) J. Org. Chem. , vol.62 , pp. 6261-6267
- Dondoni, A.¹ Marra, A.² Massi, A.³

46
- 0030798036
- (k) Oshitari, T.; Shibasaki, M.; Yoshizawa, T.; Tomita, M.; Takao, K.; Kobayashi, S. Tetrahedron 1997, 53, 10993-11006.
- (1997) Tetrahedron , vol.53 , pp. 10993-11006
- Oshitari, T.¹ Shibasaki, M.² Yoshizawa, T.³ Tomita, M.⁴ Takao, K.⁵ Kobayashi, S.⁶

47
- 0033055066
- (l) Adinolfi, M.; Barone, G.; De Lorenzo, F.; Iadonisi, A. Synlett 1999, 336-338.
- (1999) Synlett , pp. 336-338
- Adinolfi, M.¹ Barone, G.² De Lorenzo, F.³ Iadonisi, A.⁴

48
- 0011081054
- (m) I.-García, J.; C.-Flores, F. G.; H.-Mateo, F.; S.-González, F. Chem. Eur. J. 1999, 1512-1525.
- (1999) Chem. Eur. J. , pp. 1512-1525
- I-García, J.¹ C-Flores, F.G.² H-Mateo, F.³ S-González, F.⁴

49
- 12944250683
- note
- The X-ray crystallographic analysis revealed that 16 exists in a boat form See Supporting Information.

50
- 0031057009
- 20 was converted, after deprotectin, into the acetylated compound, whose structure was spectroscopically identical with that of an authentic sample. Reference: van Dorst, J. A. L. M.; van Heusden, C. J.; Tikkanen, J. M.; Kamerling, J. P.; Vliegenthart, F. G. Carbohydr. Res. 1997, 297, 209-227.
- (1997) Carbohydr. Res. , vol.297 , pp. 209-227
- Van Dorst, J.A.L.M.¹ Van Heusden, C.J.² Tikkanen, J.M.³ Kamerling, J.P.⁴ Vliegenthart, F.G.⁵

51
- 2642642035
- Reviews: (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (b) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300-2324.
- (1996) Chem. Rev. , vol.96 , pp. 443-473
- Gijsen, H.J.M.¹ Qiao, L.² Fitz, W.³ Wong, C.-H.⁴

52
- 0033549740
- Reviews: (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (b) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300-2324.
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2300-2324
- Sears, P.¹ Wong, C.-H.²

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