Efficient preparation of <em>β</em>-hydroxy aspartic acid and its derivatives

doi:10.1016/j.cclet.2018.05.012

Abstract
Figure/Table
References (0)
Related Citation (15)

Download: PDF (729 KB) HTML ( )
Export: BibTeX | EndNote (RIS)

Guide We reported an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched a-amino acid units in coralmycin A and other peptide natural products.

Abstract We report an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched α-amino acid units in coralmycin A and other peptide natural products. Fmoc and cyclic ketal-protected erythreo-β-OH-Asp 7 is prepared from cheap chiral precursor L-diethyl tartrate in six steps without the need of column purification. The modified form of 7 serves as a versatile precursor to various β-alkoxyl analogs of erythreo-β-OH-Asp. In addition, we successfully performed a model study toward the total synthesis of coralmycin A, featuring a late stage installation of the side chain primary amide group of erythreo-β-OMe-Asn.

Key words： Amino acid Natural product Erythreo-β-OH-Asp Erythreo-β-OMe-Asn Antibiotics

Received: 04 April 2018

Fund:We gratefully thank the National Natural Science Foundation of China (Nos. 21421062, 21672105, 91753124) for financial support of this work.

Corresponding Authors: Gong Chen, gongchen@nankai.edu.cn E-mail: gongchen@nankai.edu.cn

	Service

	E-mail this article
	Add to my bookshelf
	Add to citation manager
	E-mail Alert
	RSS
	Articles by authors

Cite this article:

URL:

http://www.chinchemlett.com.cn/EN/10.1016/j.cclet.2018.05.012 OR http://www.chinchemlett.com.cn/EN/Y2018/V29/I07/1113

[1]	(a) S. Baumann, J. Herrmann, R. Raju, et al., Angew. Chem. Int. Ed. 53(2014) 14605-14609;
(b)	S. Cociancich, A. Pesic, D. Petras, et al., Nat. Chem. Biol. 11(2015) 195-197.
[2]	Y.J. Kim, H.J. Kim, G.W. Kim, et al., J. Nat. Prod. 79(2016) 2223-2228.
[3]	C. Mayer, Y.L. Janin, Chem. Rev. 114(2014) 2313-2342.
[4]	(a) D.J. Payne, M.N. Gwynn, D.J. Holmes, et al., Nat. Rev. Drug. Discovery 6(2007) 29-40;
(b)	H.W. Boucher, G.H. Talbot, J.S. Bradley, et al., Clin. Infect. Dis. 48(2009) 1-12.
[5]	(a) K. Tohdo, Y. Hamada, T. Shioiri, Synapse (Hoboken, NJ, United States) 4(1994) 247-249;
(b)	M. Sendai, S. Hashiguchi, M. Tomimoto, et al., Chem. Pharm. Bull. 33(1985) 3798-3820.
[6]	(a) S.K. Jia, Y.B. Lei, L.L. Song, et al., Chin. Chem. Lett. 28(2017) 213-217;
(b)	H.T. Jiang, H.L. Gao, C.S. Ge, Chin. Chem. Lett. 28(2017) 471-475;
(c)	X. Lu, B. Xiao, R. Shang, et al., Chin. Chem. Lett. 27(2016) 305-311.
[7]	X. Huang, X. Luo, Y. Roupioz, et al., J. Org. Chem. 62(1997) 8821-8825.
[8]	Z.M. Wang, H.C. Kolb, K.B. Sharpless, J. Org. Chem. 59(1994) 5104-5105.
[9]	(a) A.M. Hafez, T. Dudding, T.R. Wagerle, et al., J. Org. Chem. 68(2003) 5819-5825;
(b)	B.M. Trost, L.R. Terrell, J. Am. Chem. Soc. 125(2003) 338-339.
[10]	K. Chen, S.Q. Zhang, H.Z. Jiang, et al., Chem.-Eur. J. 21(2015) 3264-3270.
[11]	(a) J. Deng, Y. Hamada, T. Shioiri, J. Am. Chem. Soc. 117(1995) 7824-7825;
(b)	Z. Tang, Z.H. Yang, X.H. Chen, et al., J. Am. Chem. Soc.127(2005) 9285-9289;
(c)	N. Shangguan, M. Joullie, Tetrahedron Lett. 50(2009) 6748-6750.
[12]	(a) K. Shimamoto, Y. Shigeri, Y. Yasuda-Kamatani, et al., Bioorg. Med. Chem. Lett. 10(2000) 2407-2410;
(b)	A. Wohlrab, R. Lamer, M.S. VanNieuwenhze, J. Am. Chem. Soc. 129(2007) 4175-4177.
[13]	(a) G. Campiani, M. De Angelis, S. Armaroli, et al., J. Med. Chem. 44(2001) 2507-2510;
(b)	D. Crich, A. Banerjee, J. Org. Chem. 71(2006) 7106-7109.
[14]	N. Bionda, M. Cudic, L. Barisic, et al., Amino Acids 42(2012) 285-293.
[15]	(a) D.L. Boger, R.J. Lee, P.Y. Bounaud, et al., J. Org. Chem. 65(2000) 6770-6772;
(b)	W. Jiang, J. Wanner, R.J. Lee, et al., J. Am.Chem. Soc 124(2002) 5288-5290;
(c)	W. Jiang, J. Wanner, R.J. Lee, et al., J. Am. Chem. Soc. 125(2003) 1877-1887;
(d)	D. Wong, C.M. Taylor, Tetrahedron Lett. 50(2009) 1273-1275.
[16]	J. Spengler, M. Pelay, J. Tulla-Puche, et al., Amino Acids 39(2010) 161-165.
[17]	B. Cheng, R. Muller, D. Trauner, Angew. Chem., Int. Ed. 56(2017) 12755-12759.
[18]	S. Huttel, G. Testolin, J. Herrmann, et al., Angew. Chem., Int. Ed. 56(2017) 12760-12764.
[19]	R. Hili, V. Rai, A.K. Yudin, J. Am. Chem. Soc. 132(2010) 2889-2891.
[20]	S. Saito, N. Bunya, M. Inaba, et al., Tetrahedron Lett. 26(1985) 5309-5312.
[21]	M. Tsakos, L.L. Clement, Eva S. Schaffert, et al., Angew. Chem. Int. Ed. 55(2016) 1030-1035.
[22]	B. France, V. Bruno, I. Nicolas, Tetrahedron Lett. 54(2013) 158-161.