Synthesis of Orthogonally Protected (2R,3R,4S)-4-Amino-2,3-dihydroxyheptane-1,7-dioic Acid

Abstract

(2R,3R,4S)-4-Amino-2,3-dihydroxyheptane-1,7-dioic acid, a common component of cyclic depsipeptide homophymines with anti-HIV activity, was synthesized as its orthogonally protected derivative from Fmoc-Glu(t-Bu)-OH in 6 steps. Osmium-catalyzed dihydroxylation of γ-amino-Z-α,β-unsaturated esters gave the dihydroxy esters with moderate diastereoselectivity. The stereochemistries of the amino acids­ were determined by comparison of ¹H NMR spectra.

Key words

unusual amino acid - dihydroxylation of Z-olefin - glutamic acid derivative - cyclic depsipeptide - JBCA method

• References

• 1 Zampella A, Sepe V, Lucuano P, Bellotta F, Monti MC, D’Auria MV, Jepsen T, Petek S, Andeline M.-T, Laprevote O, Aubertin A.-M, Debitus C, Poupat C, Ahond A. J. Org. Chem. 2008; 73: 5319
• 2 Zampella A, Sepe V, Bellotta F, Luciano P, D’Auria MV, Cresteil T, Debitus C, Petek S, Poupat C, Ahond A. Org. Biomol. Chem. 2009; 7: 4037
• 3 Pelay-Gimeno M, García-Ramos Y, Martin MJ, Spengler J, Molina-Guijarro JM, Munt S, Francesch AM, Cuevas C, Tulla-Puche J, Albericio F. Nat. Commun. 2013; 4: 2352
• 4 Thoen JC, Morales-Ramos AI, Lipton MA. Org. Lett. 2002; 4: 4455
• 5 Kumar AR, Rao BV. Tetrahedron Lett. 2003; 44: 5645
• 6 Zampella A, D’Auria MV, Gomez-Paloma L, Casapulla A, Debitus C, Henin Y. J. Am. Chem. Soc. 1996; 118: 6202
• 7a Kikuchi M, Konno H. Org. Lett. 2014; 16: 4324
• 7b Kikuchi M, Konno H. Heterocycles 2014; 89: 1620
• 7c Kikuchi M, Konno H. Tetrahedron 2013; 69: 7098
• 7d Kikuchi M, Nosaka K, Akaji K, Konno H. Tetrahedron Lett. 2011; 52: 3872
• 7e Konno H, Takebayashi Y, Nosaka K, Akaji K. Heterocycles 2010; 81: 79
• 7f Konno H, Aoyama S, Nosaka K, Akaji K. Synthesis 2007; 3666
• 8a Dauban P, De Saint-Fuscien C, Acher F, Prézeau L, Brabet I, Pin J-P, Dodd RH. Bioorg. Med. Chem. Lett. 2000; 10: 129
• 8b Dauban P, De Saint-Fuscien C, Dodd RH. Tetrahedron 1999; 55: 7589
• 9 Langlois N. Tetrahedron Lett. 1999; 40: 8801
• 10 Oba M, Koguchi S, Nishiyama K. Tetrahedron 2004; 60: 8089
• 11 Cahandrasekhar S, Narsihmulu Ch, Sultana SS, Reddy NR. Chem. Commun. 2003; 1716
• 12 Upadhyay P, Kumar P. Synthesis 2010; 3063
• 13 Passiniemi M, Koskinen AM. P. Synthesis 2010; 2816
• 14 Dondoni A, Merino P, Perrone D. Tetrahedron 1993; 49: 2939
• 15 Hulme AN, Montgomery CH. Tetrahedron Lett. 2003; 44: 7649
• 16 Ribes C, Falomir E, Carda M, Alberto Marco J. J. Org. Chem. 2008; 73: 7779
• 17 Azuma H, Tamagaki S, Ogino K. J. Org. Chem. 2000; 65: 3538
• 18 Yoshimitsu Y, Inuki S, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2010; 75: 3843
• 19a Ando K, Narumiya K, Takada H, Teruya T. Org. Lett. 2010; 12: 1460
• 19b Ando K. J. Synth. Org. Chem. Jpn. 2000; 58: 869
• 19c Ando K, Oishi T, Hirama M, Ohno H, Ibuka T. J. Org. Chem. 2000; 65: 4745
• 19d Ando K. J. Org. Chem. 1999; 64: 8406
• 19e Ando K. J. Org. Chem. 1998; 63: 8411
• 19f Ando K. J. Org. Chem. 1997; 62: 1934
• 19g Ando K. Tetrahedron Lett. 1995; 36: 4105
• 20 Dondoni A, Perrone D. Org. Synth. 2000; 77: 64
• 21 Tokuyama H, Yokoshima S, Lin S.-C, Li L, Fukuyama T. Synthesis 2002; 1121
• 22 Hoye AT, Wipf P. Org. Lett. 2011; 13: 2634
• 23 Han Y, Chorev M. J. Org. Chem. 1999; 64: 1972
• 24 Pihko PM, Salo TM. Tetrahedron Lett. 2003; 44: 4361
• 25 Wang L, Sharpless KB. J. Am. Chem. Soc. 1992; 114: 7568
• 26 Reetz M, Strack TJ, Mutulis F, Goddard R. Tetrahedron Lett. 1996; 52: 9293
• 27 Matsumori N, Kaneno D, Murata M, Makamura H, Tachibana K. J. Org. Chem. 1999; 64: 866
• 28 Bifulco G, Dambruoso P, Gomez-Paloma L, Riccio R. Chem. Rev. 2007; 107: 3744
• 29 Bassarello C, Bifulco G, Evidente A, Riccio R, Gomez-Paloma L. Tetrahedron Lett. 2001; 42: 8611
• 30 Krysan DJ, Rockway TW, Haight AR. Tetrahedron: Asymmetry 1994; 5: 625
• 31 Jeon J, Hong S.-K, Oh JS, Kim YG. J. Org. Chem. 2006; 71: 3310
• 32 Oh JS, Jeon J, Park DY, Kim YG. Chem. Commun. 2005; 770