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Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5401-5409

Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4 R)-2-amino-4-hydroxyadipic acid (Ahad)

(2) Yadav, Saroj a Taylor, Carol M a

a LOUISIANA STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS;

ALLYLOXYCARBONYL; ASYMMETRIC CONJUGATE ADDITION; BUILDING BLOCKES; INTRAMOLECULAR CONJUGATE ADDITION; PROTECTING GROUP; TERT-BUTYL ESTERS; TERT-BUTYLDIMETHYLSILYL; UNSATURATED ESTERS;

ESTERS;

2 AMINO 4 HYDROXYADIPIC ACID; 2 AMINO ADIPIC ACID; ADIPIC ACID DERIVATIVE; HYDROXYL GROUP; NITROGEN; OXYGEN; PROLINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; COVALENT BOND; STEREOCHEMISTRY; SYNTHESIS;

EID: 84879317942 PISSN: 00223263 EISSN: 15206904 Source Type: Journal
DOI: 10.1021/jo400558t Document Type: Article

Times cited : (13)

References (49)

1
- 0024598229
- Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Wälchli, M. J. Am. Chem. Soc. 1989, 111, 2582-2588
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 2582-2588
- Matsunaga, S.¹ Fusetani, N.² Hashimoto, K.³ Wälchli, M.⁴

2
- 0028945772
- Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 1177-1181
- (1995) J. Org. Chem. , vol.60 , pp. 1177-1181
- Matsunaga, S.¹ Fusetani, N.²

3
- 0032866563
- Wada, S.; Matsunaga, S.; Fusetani, N.; Watabe, S. Marine Biotechnol. 1999, 1, 337-341
- (1999) Marine Biotechnol. , vol.1 , pp. 337-341
- Wada, S.¹ Matsunaga, S.² Fusetani, N.³ Watabe, S.⁴

4
- 0036874977
- Wada, S.; Kantha, S. S.; Yamashita, T.; Matsunaga, S.; Fusetani, N.; Watabe, S. Marine Biotechnol. 2002, 4, 571-582
- (2002) Marine Biotechnol. , vol.4 , pp. 571-582
- Wada, S.¹ Kantha, S.S.² Yamashita, T.³ Matsunaga, S.⁴ Fusetani, N.⁵ Watabe, S.⁶

5
- 0028132715
- Bewley, C. A.; Faulkner, D. J. J. Org. Chem. 1994, 59, 4849-4852
- (1994) J. Org. Chem. , vol.59 , pp. 4849-4852
- Bewley, C.A.¹ Faulkner, D.J.²

6
- 33751156310
- Bewley, C. A.; Faulkner, D. J. J. Org. Chem. 1995, 60, 2644
- (1995) J. Org. Chem. , vol.60 , pp. 2644
- Bewley, C.A.¹ Faulkner, D.J.²

7
- 0001475887
- Schmidt, E. W.; Bewley, C. A.; Faulkner, D. J. J. Org. Chem. 1998, 63, 1254-1258
- (1998) J. Org. Chem. , vol.63 , pp. 1254-1258
- Schmidt, E.W.¹ Bewley, C.A.² Faulkner, D.J.³

8
- 0029794187
- Bewley, C. A.; Holland, N. D.; Faulkner, D. J. Experientia 1996, 52, 716-722
- (1996) Experientia , vol.52 , pp. 716-722
- Bewley, C.A.¹ Holland, N.D.² Faulkner, D.J.³

9
- 0000693758
- Schmidt, E. W.; Obraztsova, A. Y.; Davidson, S. K.; Faulkner, D. J.; Haygood, M. G. Marine Biol. 2000, 136, 969-977
- (2000) Marine Biol. , vol.136 , pp. 969-977
- Schmidt, E.W.¹ Obraztsova, A.Y.² Davidson, S.K.³ Faulkner, D.J.⁴ Haygood, M.G.⁵

10
- 64349112353
- Ho, C. H.; Magtanong, L.; Barker, S. L.; Gresham, D.; Nishimura, S.; Natarajan, P.; Koh, J. L. Y.; Porter, J.; Gray, C. A.; Andersen, R. J.; Giaever, G.; Nislow, C.; Andrews, B.; Botstein, D.; Graham, T. R.; Yoshida, M.; Boone, C. Nat. Biotechnol. 2009, 27, 369-377
- (2009) Nat. Biotechnol. , vol.27 , pp. 369-377
- Ho, C.H.¹ Magtanong, L.² Barker, S.L.³ Gresham, D.⁴ Nishimura, S.⁵ Natarajan, P.⁶ Koh, J.L.Y.⁷ Porter, J.⁸ Gray, C.A.⁹ Andersen, R.J.¹⁰ Giaever, G.¹¹ Nislow, C.¹² Andrews, B.¹³ Botstein, D.¹⁴ Graham, T.R.¹⁵ Yoshida, M.¹⁶ Boone, C.¹⁷

11
- 77953810135
- Nishimura, S.; Arita, Y.; Honda, M.; Iwamoto, K.; Matsuyama, A.; Shirai, A.; Kawasaki, H.; Kakeya, H.; Kobayashi, T.; Matsunaga, S.; Yoshida, M. Nat. Chem. Biol. 2010, 6, 519-526
- (2010) Nat. Chem. Biol. , vol.6 , pp. 519-526
- Nishimura, S.¹ Arita, Y.² Honda, M.³ Iwamoto, K.⁴ Matsuyama, A.⁵ Shirai, A.⁶ Kawasaki, H.⁷ Kakeya, H.⁸ Kobayashi, T.⁹ Matsunaga, S.¹⁰ Yoshida, M.¹¹

12
- 0025893791
- Tserng, K. Y.; Jin, S. J. Biochemistry 1991, 30, 2508-2514
- (1991) Biochemistry , vol.30 , pp. 2508-2514
- Tserng, K.Y.¹ Jin, S.J.²

13
- 0021906512
- Svendsen, J. S.; Whist, J. E.; Sydnes, L. K. J. Chromatogr. B 1985, 337, 9-19
- (1985) J. Chromatogr. B , vol.337 , pp. 9-19
- Svendsen, J.S.¹ Whist, J.E.² Sydnes, L.K.³

14
- 0015818228
- Fellows, F. C. I.; Lewis, M. H. R. Biochem. J. 1973, 136, 329-334
- (1973) Biochem. J. , vol.136 , pp. 329-334
- Fellows, F.C.I.¹ Lewis, M.H.R.²

15
- 84982335161
- Blass, J.; Macheboeuf, M. Helv. Chim. Acta 1946, 29, 1315-1317
- (1946) Helv. Chim. Acta , vol.29 , pp. 1315-1317
- Blass, J.¹ Macheboeuf, M.²

16
- 0000615552
- Kristensen, E. P.; Larsen, L. M.; Olsen, O.; Sørensen, H. Acta Chem. Scand. B 1980, B34, 497-504
- (1980) Acta Chem. Scand. B , vol.34 , pp. 497-504
- Kristensen, E.P.¹ Larsen, L.M.² Olsen, O.³ Sørensen, H.⁴

17
- 0001617775
- Benoiton, L.; Winitz, M.; Birnbaum, S. M.; Greenstein, J. P. J. Am. Chem. Soc. 1957, 79, 6192-6198
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 6192-6198
- Benoiton, L.¹ Winitz, M.² Birnbaum, S.M.³ Greenstein, J.P.⁴

18
- 0342768253
- Tohdo, K.; Hamada, Y.; Shioiri, T. Synlett 1994, 105-106
- (1994) Synlett , pp. 105-106
- Tohdo, K.¹ Hamada, Y.² Shioiri, T.³

19
- 0004164065
- Tohdo, K.; Hamada, Y.; Shioiri, T. Pept. Chem. 1991, 7-12
- (1991) Pept. Chem. , pp. 7-12
- Tohdo, K.¹ Hamada, Y.² Shioiri, T.³

20
- 85048834906
- Tohdo, K.; Hamada, Y.; Shioiri, T. Synlett 1994, 247-249
- (1994) Synlett , pp. 247-249
- Tohdo, K.¹ Hamada, Y.² Shioiri, T.³

21
- 66249111130
- Edagwa, B. J.; Taylor, C. M. J. Org. Chem. 2009, 74, 4132-4136
- (2009) J. Org. Chem. , vol.74 , pp. 4132-4136
- Edagwa, B.J.¹ Taylor, C.M.²

22
- 84981467418
- Michl, K. Liebigs Ann. Chem. 1981, 33-39
- (1981) Liebigs Ann. Chem. , pp. 33-39
- Michl, K.¹

23
- 0000234063
- Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 12414-12415
- Corey, E.J.¹ Xu, F.² Noe, M.C.³

24
- 0030659804
- Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598
- (1997) Tetrahedron Lett. , vol.38 , pp. 8595-8598
- Lygo, B.¹ Wainwright, P.G.²

25
- 37049088446
- Lee, S. S.; Li, Z.-H.; Lee, D. H.; Kim, D. H. J. Chem. Soc., Perkin Trans. 1 1995, 2877-2882
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 2877-2882
- Lee, S.S.¹ Li, Z.-H.² Lee, D.H.³ Kim, D.H.⁴

26
- 0025677294
- Bellamy, F. D.; Bondoux, M.; Dodey, P. Tetrahedron Lett. 1990, 31, 7323-7326
- (1990) Tetrahedron Lett. , vol.31 , pp. 7323-7326
- Bellamy, F.D.¹ Bondoux, M.² Dodey, P.³

27
- 0000749329
- Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389-1392
- (1984) Chem. Lett. , pp. 1389-1392
- Saito, S.¹ Hasegawa, T.² Inaba, M.³ Nishida, R.⁴ Fujii, T.⁵ Nomizu, S.⁶ Moriwake, T.⁷

28
- 0344875940
- Zhu, J.; Ma, D. Angew. Chem., Int. Ed. 2003, 42, 5348-5351
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5348-5351
- Zhu, J.¹ Ma, D.²

29
- 71549146867
- Allepuz, A. C.; Badorrey, R.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Eur. J. Org. Chem. 2009, 6172-6178
- (2009) Eur. J. Org. Chem. , pp. 6172-6178
- Allepuz, A.C.¹ Badorrey, R.² Díaz-De-Villegas, M.D.³ Gálvez, J.A.⁴

30
- 33746326181
- Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328-9329
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 9328-9329
- Chen, Y.K.¹ Yoshida, M.² Macmillan, D.W.C.³

31
- 0000458865
- Stambouli, A.; Amouroux, R.; Chastrette, M. Tetrahedron Lett. 1987, 28, 5301-5302
- (1987) Tetrahedron Lett. , vol.28 , pp. 5301-5302
- Stambouli, A.¹ Amouroux, R.² Chastrette, M.³

32
- 0037170894
- Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533-2549
- (2002) Tetrahedron , vol.58 , pp. 2533-2549
- Satoh, T.¹ Hanaki, N.² Kuramochi, Y.³ Inoue, Y.⁴ Hosoya, K.⁵ Sakai, K.⁶

33
- 3643083611
- Iesce, M. R.; Cermola, F.; Guitto, A.; Scarpati, R.; Graziano, M. L. J. Org. Chem. 1995, 60, 5324-5327
- (1995) J. Org. Chem. , vol.60 , pp. 5324-5327
- Iesce, M.R.¹ Cermola, F.² Guitto, A.³ Scarpati, R.⁴ Graziano, M.L.⁵

34
- 33847029577
- Vesely, J.; Ibrahem, I.; Rios, R.; Zhao, G.-L.; Xu, Y.; Córdova, A. Tetrahedron Lett. 2007, 48, 2193-2198
- (2007) Tetrahedron Lett. , vol.48 , pp. 2193-2198
- Vesely, J.¹ Ibrahem, I.² Rios, R.³ Zhao, G.-L.⁴ Xu, Y.⁵ Córdova, A.⁶

35
- 0001218250
- Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181-4184
- (2001) Org. Lett. , vol.3 , pp. 4181-4184
- Sibi, M.P.¹ Liu, M.²

36
- 0026770305
- Kundu, B. Tetrahedron Lett. 1992, 33, 3193-3196
- (1992) Tetrahedron Lett. , vol.33 , pp. 3193-3196
- Kundu, B.¹

37
- 0035945982
- Somogyi, L.; Haberhauer, G.; Rebek, J., Jr. Tetrahedron 2001, 57, 1699-1708
- (2001) Tetrahedron , vol.57 , pp. 1699-1708
- Somogyi, L.¹ Haberhauer, G.² Rebek Jr., J.³

38
- 0031007071
- Chen, W.-C.; Vera, M. D.; Joullié, M. M. Tetrahedron Lett. 1997, 38, 4025-4028
- (1997) Tetrahedron Lett. , vol.38 , pp. 4025-4028
- Chen, W.-C.¹ Vera, M.D.² Joullié, M.M.³

39
- 0025036824
- Li, W.-R.; Ewing, W. R.; Harris, B. D.; Joullié, M. M. J. Am. Chem. Soc. 1990, 112, 7659-7672
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 7659-7672
- Li, W.-R.¹ Ewing, W.R.² Harris, B.D.³ Joullié, M.M.⁴

40
- 0000997336
- Stevens, C. M.; Watanabe, R. J. Am. Chem. Soc. 1950, 72, 725-727
- (1950) J. Am. Chem. Soc. , vol.72 , pp. 725-727
- Stevens, C.M.¹ Watanabe, R.²

41
- 65949102995
- Hachisako, H.; Ryu, N.; Murakami, R. Org. Biomol. Chem. 2009, 7, 2327-2337
- (2009) Org. Biomol. Chem. , vol.7 , pp. 2327-2337
- Hachisako, H.¹ Ryu, N.² Murakami, R.³

42
- 80052440278
- For specific application of this strategy to α-AAA, see the Supporting Information in: Zhang, Y.; Lu, H.; Lin, Y.; Cheng, J. Macromolecules 2011, 44, 6641-6644.
- (2011) Macromolecules , vol.44 , pp. 6641-6644
- Zhang, Y.¹ Lu, H.² Lin, Y.³ Cheng, J.⁴

43
- 37049091466
- Baldwin, J. E.; Herchen, S. R.; Johnson, B. L.; Jung, M.; Usher, J. J.; Wan, T. J. Chem. Soc., Perkin Trans. 1 1981, 2253-2257
- (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 2253-2257
- Baldwin, J.E.¹ Herchen, S.R.² Johnson, B.L.³ Jung, M.⁴ Usher, J.J.⁵ Wan, T.⁶

44
- 4544226585
- Grummitt, A. R.; Rutledge, P. J.; Clifton, I. J.; Baldwin, J. E. Biochem. J. 2004, 382, 659-666
- (2004) Biochem. J. , vol.382 , pp. 659-666
- Grummitt, A.R.¹ Rutledge, P.J.² Clifton, I.J.³ Baldwin, J.E.⁴

45
- 14844299308
- Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378-1382
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1378-1382
- Nicolaou, K.C.¹ Estrada, A.A.² Zak, M.³ Lee, S.H.⁴ Safina, B.S.⁵

46
- 37049137658
- Hussein, S. A. M.; Ollis, W. D.; Smith, C.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. I 1975, 1480-1492
- (1975) J. Chem. Soc., Perkin Trans. i , pp. 1480-1492
- Hussein, S.A.M.¹ Ollis, W.D.² Smith, C.³ Stoddart, J.F.⁴

47
- 0035806270
- Luo, Y.; Evindar, D. F.; Lajoie, G. A. Tetrahedron Lett. 2001, 42, 3807-3809
- (2001) Tetrahedron Lett. , vol.42 , pp. 3807-3809
- Luo, Y.¹ Evindar, D.F.² Lajoie, G.A.³

48
- 33845273267
- Wender, P. A.; Horan, J. C.; Verma, V. A. Org. Lett. 2006, 8, 5299-5302
- (2006) Org. Lett. , vol.8 , pp. 5299-5302
- Wender, P.A.¹ Horan, J.C.² Verma, V.A.³

49
- 49649093144
- Wender, P. A.; Verma, V. A. Org. Lett. 2008, 10, 3331-3334
- (2008) Org. Lett. , vol.10 , pp. 3331-3334
- Wender, P.A.¹ Verma, V.A.²

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