A Versatile Approach to Noncoded β-Hydroxy-α-amino Esters and α-Amino Acids/Esters from Morita–Baylis–Hillman Adducts

Hamid Ullah; André V. Ferreira; José A. Bendassolli; Manoel T. Rodrigues Jr.; André Luiz B. Formiga; Fernando Coelho

doi:10.1055/s-0034-1379168

Synthesis, Table of Contents

Synthesis 2015; 47(01): 113-123
DOI: 10.1055/s-0034-1379168

paper

A Versatile Approach to Noncoded β-Hydroxy-α-amino Esters and α-Amino Acids/Esters from Morita–Baylis–Hillman Adducts

Hamid Ullah

^aUniversity of Campinas, Institute of Chemistry, Laboratory of Synthesis of Natural Products and Drugs, P. O. Box 6154, 13083-970 Campinas, SP, Brazil

,

André V. Ferreira

^aUniversity of Campinas, Institute of Chemistry, Laboratory of Synthesis of Natural Products and Drugs, P. O. Box 6154, 13083-970 Campinas, SP, Brazil

^bCenter for Nuclear Energy, University of São Paulo – CENA/USP, Stable Isotopes Laboratory, P. O. Box 96, 13400-970 Piracicaba, SP, Brazil

,

José A. Bendassolli

^bCenter for Nuclear Energy, University of São Paulo – CENA/USP, Stable Isotopes Laboratory, P. O. Box 96, 13400-970 Piracicaba, SP, Brazil

,

Manoel T. Rodrigues Jr.

^aUniversity of Campinas, Institute of Chemistry, Laboratory of Synthesis of Natural Products and Drugs, P. O. Box 6154, 13083-970 Campinas, SP, Brazil

,

André Luiz B. Formiga

^cUniversity of Campinas, Institute of Chemistry, Laboratory of Coordination Chemistry, P. O. Box 6154, 13083-970 Campinas, SP, Brazil Fax: +55(19)37883023 Email: coelho@iqm.unicamp.br

,

Fernando Coelho*

^aUniversity of Campinas, Institute of Chemistry, Laboratory of Synthesis of Natural Products and Drugs, P. O. Box 6154, 13083-970 Campinas, SP, Brazil

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Abstract

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Abstract

A simple and straightforward approach to the diastereoselective synthesis of noncoded β-hydroxy-α-amino esters from Morita–Baylis–Hillman (MBH) adducts is described. The strategy is based on a one-pot sequence involving an oxidative cleavage of the double bond of silylated Morita–Baylis–Hillman adducts, followed by the reaction with hydroxylamine hydrochloride/pyridine to form oximes. The stereoselective reduction of the oximes with the mixture MoCl₅·nH₂O/NaBH₃CN led to the corresponding anti-β-hydroxy-α-amino esters in four steps in good overall yield and with diastereoselectivity higher than 95%. A slight modification of the synthetic approach has allowed for the racemic synthesis of a set of noncoded α-amino esters/acids and DOPA.

Key words

Morita–Baylis–Hillman adducts - amino acids - reduction - diastereoselectivity - DOPA

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References

References

1a Ludlow BS, Villo P, Somfai P. Chem. Eur. J. 2012; 18: 7219
1b Van der Berg RJ. B. H. N, Van den Helst H, Korevaar CG. N, Aerts JM. F. G, Van der Marel GA, Overkleeft HS. Eur. J. Org. Chem. 2011; 6685 ; and references cited therein
1c Fesko K, Giger L, Hilvert D. Bioorg. Med. Chem Lett. 2008; 18: 5987

2a Ludlow BS, Villo P, Hacker C. Org. Lett. 2010; 12: 5274
2b Rama Rao AV, Chakraborty TK, Laxmareddy K, Srinivasa Rao A. Tetrahedron Lett. 1994; 35: 5043
2c Willis MC, Cutting GA, Piccio VD, Durbin MJ, John MP. Angew. Chem. Int Ed. 2005; 44: 1543

3 Shin-Ya K, Kim J.-S, Furihata K, Hayakawa Y, Seto H. Tetrahedron Lett. 1997; 38: 7079

4a Shin-Ya K, Kim J.-S, Hayakawa Y, Seto H. J. Neurochem. 1999; 73: S190
4b Limon A, Reyes-Ruiz JM, Vaswani RG, Chamberlin AR, Miledi R. ACS Chem. Neurosci. 2010; 1: 175
4c Ahmed AH, Hamada M, Shinada T, Ohfune Y, Weerasinghe L, Garner PP, Oswald RE. J. Biol. Chem. 2012; 287: 41007

For some recent examples concerning the total synthesis of kaitocephalin, see:

4d Lee W, Youn JH, Kang SH. Chem. Commun. 2013; 49: 5231
4e Takahashi H, Yamaguchi D, Ishihara J, Hatakeyama S. Org. Lett. 2012; 14: 1644
4f Vaswani RG, Chamberlin AR. J. Org. Chem. 2008; 73: 1661
4g Kawasaki M, Shinada T, Hamada M, Ohfune Y. Org. Lett. 2005; 7: 4165
4h Watanabe H, Okue M, Kobayashi H, Kitahara T. Tetrahedron Lett. 2002; 43: 861
4i Ma DW, Yang JD. J. Am. Chem. Soc. 2001; 123: 9706

5a Miyabe Y, Kozutsumi Y, Nakamura S, Fujita T, Kawasaki T. Biochem. Biophys. Res. Commun. 1995; 211: 396
5b Horn WS, Smith JL, Bitts GF, Raghoobar SL, Helms GL, Kurtz MB, Marrinan JA, Frommer BR, Thornton RA, Mandala SM. J. Antibiot. 1992; 45: 1692

For some recent examples related to the total synthesis of sphingofungin E, see:

5c Martinkova M, Gonda J, Raschmanova JS, Slaninkova M, Kuchar J. Carbohydr. Res. 2010; 345: 2427
5d Ohfune Y, Shinada T. Eur. J. Org. Chem. 2005; 5127
5e Kang SH, Kang SY, Lee HS, Burlass AJ. Chem. Rev. 2005; 105: 4537
5f Nakamura T, Shiozaki M. Tetrahedron 2002; 58: 8779
5g Oishi T, Ando K, Inomiya K, Sato H, Iida M, Chida N. Bull. Soc. Chim. Jpn. 2002; 75: 1927
5h Oishi T, Ando K, Inomiya K, Sato H, Iida M, Chida N. Org. Lett. 2002; 4: 151
5i Nakamura T, Shiozaki M. Tetrahedron Lett. 2001; 42: 2701
5j Wang B, Yu XM, Lin GQ. Synlett 2001; 904

6 Takahashi A, Kurasawa S, Ikeda D, Okami Y, Takeuchi J. J. Antibiot. 1989; 42: 1556

7a Renner MK, Shen Y.-C, Cheng X.-C, Jensen PR, Frankmoelle W, Kauffman CA, Fenical W, Lobkovsky E, Clardy J. J. Am. Chem. Soc. 1999; 121: 11273
7b Wen S.-J, Hu T.-S, Yao Z.-J. Tetrahedron 2005; 61: 4931

For some examples concerning the total synthesis of cyclomarins, see:

7c Hansen DB, Lewis AS, Gavalas SJ, Joulie MM. Tetrahedron: Asymmetry 2006; 17: 15
7d Hansen DB, Joulie MM. Tetrahedron: Asymmetry 2005; 16: 3963
7e Hansen DB, Starr ML, Tolstoy N, Joulie MM. Tetrahedron: Asymmetry 2005; 16: 3623
7f Tarver JE, Terranova KM, Joulie MA. Tetrahedron 2004; 60: 10277
7g Wen S.-J, Yao Z.-J. Org. Lett. 2004; 6: 2721
7h Sugiyama H, Shioiri T, Yokokawa F. Tetrahedron Lett. 2002; 43: 3489

8 Shen H.-Y, Tian G.-L, Ye Y.-H, Wang J. J. Mol. Catal. B 2005; 37: 26
9 Paioti PH. S, Rezende P, Coelho F. J. Braz. Chem. Soc. 2012; 23: 285 ; Chem. Abstr. 2012, 156, 492800

For isolation and biological effects of (+)-lactacystin, see:

10a Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka H, Sasaki Y. J. Antibiot. 1991; 44: 113
10b Fenteany G, Standaert RF, Lane WS, Choi S, Corey EJ, Schreiber SL. Science 1995; 268: 726
10c Craiu A, Gaczynska M, Akopian T, Gramm CF, Fenteany G, Goldberg AL, Rock KL. J. Biol. Chem. 1997; 272: 13437
10d Orlowski RZ. Cell. Death Differ. 1999; 6: 303

For some outstanding examples concerning the total synthesis of (+)-lactacystin, see:

10e Corey EJ, Reichard GA. J. Am. Chem. Soc. 1992; 114: 10677
10f Nagamitsu T, Sunazuka T, Tanaka H, Omura S, Sprergeler PA, Smith III AB. J. Am. Chem. Soc. 1996; 118: 3584
10g Panek JS, Masse CE. Angew. Chem. Int. Ed. 1999; 38: 1093
10h Shibasaki M, Kanai M, Fukuda N. Chem. Asian J. 2007; 2: 20

11 Li Q, Yang SB, Zhang S, Li L, Fei XP. J. Org. Chem. 2009; 74: 1627

12a Kobayashi J, Nakamura M, Mori Y, Yamashita Y, Kobayashi S. J. Am. Chem. Soc. 2004; 126: 9192
12b Crich D, Banerjee A. J. Org. Chem. 2006; 71: 7106

13a Najera C, Sansano JM. Chem. Rev. 2007; 107: 4584
13b Bergmeier SC. Tetrahedron 2000; 56: 2561
13c Ager DJ, Prakash I, Schaad DR. Chem. Rev. 1996; 106: 835

14a Schöllkopf U, Hartig W, Groth U. Angew. Chem., Int. Ed. Engl. 1980; 19: 212
14b Belokon YN, Bulychev AG, Vitt SV, Struchkov YT, Batsanov AS, Timofeeva TV, Tsyryapkin VA, Ryzhov MG, Lysova LA. J. Am. Chem. Soc. 1985; 107: 4252
14c MacMillan JB, Molinski TF. Org. Lett. 2002; 4: 1883
14d Thayumanavan R, Tanaka F, Barbas CF. Org. Lett. 2004; 6: 3541
14e Willis MC, Cutting GA, Piccio VJ. D, Durbin MJ, John BM. P. Angew. Chem. Int. Ed. 2005; 44: 1543
14f Ma B, Parkinson JL, Castle SL. Tetrahedron Lett. 2007; 48: 2083
14g Patel J, Clavé G, Renard P.-Y, Franck X. Angew. Chem. Int. Ed. 2008; 47: 4224
14h Jackson BG, Pedersen SW, Fisher JW, Misner JW, Gardner JP, Staszak MA, Doecke C, Rizzo J, Aikins J, Farkas E, Trinkle KL, Vicenzi J, Reinhard M, Kroeff EP, Higginbotham CA, Gazak RJ, Zhang TY. Tetrahedron 2000; 56: 5667
14i Steinreber J, Fesko K, Reisinger C, Schürmann M, van Assema F, Wolberg M, Mink D, Griengl DH. Tetrahedron 2007; 63: 918
14j Steinreber J, Fesko K, Mayer C, Reisinger C, Schürmann M, Griengl H. Tetrahedron 2007; 63: 8088
14k Fesko K, Uhl M, Steinreber J, Gruber K, Griengl H. Angew. Chem. Int. Ed. 2010; 49: 121
14l Sagui F, Conti P, Roda G, Contestabile R, Riva S. Tetrahedron 2008; 64: 5079
14m Fesko K, Giger L, Hilvert D. Bioorg. Med. Chem. Lett. 2008; 18: 5987
14n Li Q, Yang S.-B, Zhang Z, Li L, Xu P.-F. J. Org. Chem. 2009; 74: 1627
14o Sladojevich F, Trabocchi A, Guarna A, Dixon DJ. J. Am. Chem. Soc. 2011; 133: 1710

15 Davis FA, Srirajan V, Fanelli DL, Portonovo P. J. Org. Chem. 2000; 65: 7663 ; and references cited therein
16 Alonso M, Riera A. Tetrahedron: Asymmetry 2005; 16: 3908 ; and references cited therein

17a Morgan AJ, Masse CE, Panek JS. Org. Lett. 1999; 1: 1949
17b Zhang H, Xia P, Zhou W. Tetrahedron: Asymmetry 2000; 11: 3439
17c Park H, Cao B, Joullié MM. J. Org. Chem. 2001; 66: 7223
17d Davies SG, Fletcher AM, Frost AB, Lee JA, Roberts PM, Thomson JE. Tetrahedron 2013; 69: 8885

18a Jackson RF. W, Palmer NJ, Whythes MJ, Clegg W, Elsegood MR. J. J. Org. Chem. 1995; 60: 6431
18b Genet J.-P. Pure Appl. Chem. 1996; 68: 593
18c Sugisaki CH, Carroll PJ, Correia CR. D. Tetrahedron Lett. 1998; 39: 3413
18d Kumar TP, Chandrasekhar S. Synthesis 2012; 44: 2889

19a Alker D, Hamblett G, Harwood LM, Robertson SM, Walkin DJ, Williams CE. Tetrahedron 1998; 54: 6089
19b Aldous DJ, Drew MG. B, Draffin WN, Hamelin EM. N, Harwood LM, Thurairatnam S. Synthesis 2005; 3271
19c Seashore-Ludlow B, Torssell S, Somfai P. Eur. J. Org. Chem. 2010; 3927

20a Malkino K, Goto T, Hiroki Y. Angew. Chem. Int. Ed. 2004; 43: 882
20b Noyori R, Ikeda T, Ohkuma T, Wildham M, Kitamura M, Takaya H, Akutagawa S, Sayo N, Saito T. J. Am. Chem. Soc. 1989; 111: 9134
20c Lei A, Wu S, He M, Zhang X. J. Am. Chem. Soc. 2004; 126: 1626
20d Hamada Y, Koseki Y, Fujii T, Maeda T, Hibino T, Makino K. Chem. Commun. 2008; 6206
20e Liu ZQ, Schultz CS, Sherwood CA, Krska S, Dormer PG, Desmond R, Lee C, Sherer EC, Shpungin J, Cuff J, Xu F. Tetrahedron Lett. 2011; 52: 1685
20f Seashore-Ludlow B, Saint-Dizier F, Somfai P. Org. Lett. 2012; 14: 6334 ; and references cited therein

21 Hernadez-Juan FA, Richardson RD, Dixon DJ. Synlett 2006; 2673

22a Griesbeck AG, Bondock S, Lex J. J. Org. Chem. 2003; 68: 9899
22b Huang CM, Jiang H, Wang RZ, Quah CK, Fun HK, Zhang Y. Org. Biomol. Chem. 2013; 11: 5023

23 Tomasini C, Vecchione A. Org. Lett. 1999; 1: 2153
24 Fanning KN, Jamieson AG, Sutherland A. Org. Biomol. Chem. 2005; 3: 3749

25a Tellam JP, Kociock-Köhn G, Carbery DR. Org. Lett. 2008; 10: 5199
25b Tellam JP, Carbery DR. J. Org. Chem. 2010; 75: 7809
25c Tellam JP, Carbery DR. Tetrahedron Lett. 2011; 52: 6027

26a Boukhris S, Souizi A. Tetrahedron Lett. 1999; 40: 1669
26b Miyata O, Asai H, Nato T. Chem. Pharm. Bull. 2005; 53: 355

27a Mateus CR, Almeida WP, Coelho F. Tetrahedron Lett. 2000; 41: 2533
27b Mateus CR, Feltrin MP, Costa AM, Coelho F, Almeida WP. Tetrahedron 2001; 57: 6901
27c Bouzide A. Org. Lett. 2002; 4: 1347
27d Coelho F, Almeida WP, Mateus CR, Furtado LD, Gouveia JC. F. ARKIVOC 2003; (x): 443
27e Gomaa MS, Bridgens CE, Aboraia AS, Veal GJ, Redfern CP. F, Brancale A, Amstrong JL, Simmons C. J. Med. Chem. 2011; 54: 2778
27f Porto RS, Vasconcellos ML. A. A, Ventura E, Coelho F. Synthesis 2005; 2297

28a Coelho F, Almeida WP, Veronese D, Mateus CR, Lopes EC. S, Silveira GP. C, Rossi RC, Pavam CH. Tetrahedron 2002; 58: 7437
28b Almeida WP, Coelho F. Tetrahedron Lett. 1998; 39: 8609

29a Santos MS, Coelho F. RSC Adv. 2012; 2: 3237
29b Abella CA. M, Rezende P, Lino de Souza MF, Coelho F. Tetrahedron Lett. 2008; 49: 145
29c Frezza M, Soulère L, Queneau Y, Doutheau A. Tetrahedron Lett. 2005; 46: 6495

30a Borch RF, Bernstein MD, Durst HD. J. Am. Chem. Soc. 1971; 93: 2897
30b Leeds JP, Kirst HA. Synth. Commun. 1998; 18: 777
30c Khlestkin VK, Mazhukin DG. Curr. Org. Chem. 2003; 7: 967
30d Narasaka K, Kitamura M. Eur. J. Org. Chem. 2005; 4505
30e Zeynizadeh B, Kouhkan M. Bull. Korean Soc. Chem. 2011; 32: 3448
30f Pakulski MM, Mahato SK, Boniak MJ, Kreminski MP, Zaidlewicz M. Tetrahedron: Asymmetry 2012; 23: 716
30g Breitenmoser RA, Fink T, Abele S. Org. Process Res. Dev. 2012; 16: 2008
30h Ou W, Espinosa S, Melendez HJ, Farré SM, Alvarez JL, Torres V, Martinez I, Santiago KM, Ortiz-Marciales M. J. Org. Chem. 2013; 78: 5314

31 Zeynizadeh B, Kouhkan M. Bull. Korean Soc. Chem. 2011; 32: 3323
32 In order to collect some evidences concerning the role played by TBS group on the diastereoselectivity of the oxyimino reduction, we have carried out the same sequence using PMB as protecting group. No diastereoselectivity was observed in these cases.

33a Adams ZM, Jackson RF. W, Palmer NJ, Rami HK, Whythes MJ. J. Chem. Soc., Perkin Trans. 1 1999; 937
33b Hameršak Z, Šepac D, Žiher D, Šunjić V. Synthesis 2003; 375

34a Cherest M, Felkin H, Prudent N. Tetrahedron Lett. 1968; 2199
34b Ahn NT. Top. Curr. Chem. 1980; 88: 144
34c Hoffmann RW. Chem. Rev. 1989; 89: 1841

35a Basavaiah D, Kumaragurubaran N. Tetrahedron Lett. 2001; 42: 477
35b Im YJ, Kim JM, Mun JH, Kim JN. Bull. Korean Chem. Soc. 2001; 22: 349

36 Cotzias G. N. Engl J. Med. 1968; 278: 630
37 Scriabine A. Discovery and Development of Major Drugs Currently in Use . In Pharmaceutical Innovation: Revolutionizing Human Health . Landau R, Achilladelis B, Scriabine A. Chemical Heritage Press; Philadelphia: 1999: 222-223

For outstanding examples concerning the asymmetric synthesis of l-DOPA, see:

38a Knowles WS. Acc. Chem. Res. 1983; 16: 106
38b Ooi T, Kameda M, Tannai H, Maruoka K. Tetrahedron Lett. 2000; 41: 8339
38c Huang S.-Y, Shen Y.-W, Chan H.-S. Enzyme Microb. Technol. 2002; 30: 779
38d Huang W, Taylor S, Fu K, Lin Y, Zhang D, Hanks TW, Rao AM, Sun Y.-P. Nano Lett. 2002; 2: 311
38e Seetharam G, Saville BA. Enzyme Microb. Technol. 2002; 31: 747
38f Sayed IA, Sudalai A. Tetrahedron: Asymmetry 2004; 15: 3111
38g Vald RH. D, Puzer L, Gomes JM, Marques CE. S. J, Aranda DA. G, Bastos ML, Gemal AL, Antunes OA. C. Catal. Commun. 2004; 5: 631
38h Koyanagi T, Katayama T, Suzuki H, Nakazawa H, Yokozeki K, Kumagai H. J. Biotechnol. 2005; 115: 303
38i Ates S, Cortenlioglu E, Bayraktar E, Mehmetoglu V. Enzyme Microb. Technol. 2007; 40: 683
38j Min K, Park D.-H, Yoo YJ. J. Biotechnol. 2010; 146: 40

39 Kitagawa T, Kawaguchi M, Inoue S, Katayama S. Chem. Pharm. Bull. 1991; 39: 3030
40 Adamo C, Barone V. J. Chem. Phys. 1999; 110: 6158
41 Cramer CJ, Truhlar DG. Phys. Chem. Chem. Phys. 2009; 11: 10757
42 Hay PJ, Wadt WR. J. Chem. Phys. 1985; 82: 299

43a Ditchfie R, Hehre WJ, Pople JA. J. Chem. Phys. 1971; 54: 724
43b Hehre WJ, Ditchfie R, Pople JA. J. Chem. Phys. 1972; 56: 2257
43c Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS, Defrees DJ, Pople JA. J. Chem. Phys. 1982; 77: 3654
43d Harihara P, Pople JA. Theor. Chim. Acta 1973; 28: 213

44 Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA. J. Comput. Chem. 1993; 14: 1347
45 JMOL: an open-source Java viewer for chemical structures in 3D. See: http://www.jmol.org.

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