Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(23): 3276-3280
DOI: 10.1055/s-0033-1338545
DOI: 10.1055/s-0033-1338545
paper
Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine
Further Information
Publication History
Received: 27 August 2013
Accepted after revision: 13 September 2013
Publication Date:
26 September 2013 (online)
Abstract
An efficient and stereoselective synthesis of (+)-polyoxamic acid was developed. The route starts with the commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, a substance that has not been used previously as a starting material for the preparation of this target. The route also features the use of a stereocontrolled Sharpless asymmetric dihydroxylation reaction, promoted by AD-mix-α, which is followed by a regioselective aziridine ring-opening process, to generate the basic skeleton of target natural product. Subsequent oxidation and global deprotection produces (+)-polyoxamic acid.
-
References
- 1a Isono K, Asahi K, Suzuki S. J. Am. Chem. Soc. 1969; 91: 7490
- 1b Isono K, Suzuki S. Heterocycles 1979; 13: 333
- 2a Naider F, Shenbagamurthi P, Steinfeld AS, Smith HA, Boney C, Becker JM. Antimicrob. Agents Chemother. 1983; 24: 787
- 2b Shenbagamurthi P, Smith HA, Becker JM, Naider F. J. Med. Chem. 1986; 29: 802
- 3 Lee YJ, Park Y, Kim MH, Jew SS, Park HG. J. Org. Chem. 2011; 76: 740
- 4 Trost BM, Krueger AC, Bunt RC, Zambrano J. J. Am. Chem. Soc. 1996; 118: 6520
- 5 Enders D, Vrettou M. Synthesis 2006; 2155
- 6a Savage I, Thomas E. J. Chem. Soc., Chem. Commun. 1989; 717
- 6b Savage I, Thomas EJ, Wilson PD. J. Chem. Soc., Perkin Trans. 1 1999; 3291
- 7 Kim KS, Lee YJ, Kim JH, Sung DK. Chem. Commun. 2002; 1116
- 8 Raghavan S, Joseph SC. Tetrahedron Lett. 2003; 44: 6713
- 9 Matsuura F, Hamada Y, Shioiri T. Tetrahedron Lett. 1994; 35: 733
- 10 Veeresa G, Datta A. Tetrahedron Lett. 1998; 39: 119
- 11 Yoon HJ, Kim YW, Lee BK, Lee WK, Kim Y, Ha HJ. Chem. Commun. 2007; 79
- 12 Righi G, Mandic' E, Naponiello GC. M, Bovicelli P, Tirotta I. Tetrahedron 2012; 68: 2984
- 13 Lee BK, Choi HG, Roh EJ, Lee WK, Sim T. Tetrahedron Lett. 2013; 54: 553
- 14 Watson AA, Fleet GW. J, Asano N, Molyneux RJ, Nash RJ. Phytochemistry 2001; 56: 265
- 15 Choi SK, Lee JS, Kim JH, Lee WK. J. Org. Chem. 1997; 62: 743
- 16 Andres JM, de Elena N, Pedrosa R. Tetrahedron 2000; 56: 1523
- 17 Ratcliff R, Rodehors R. J. Org. Chem. 1970; 35: 4000
- 18 Barfoot CW, Harvey JE, Kenworthy MN, Kilburn JP, Ahmed M, Taylor RJ. K. Tetrahedron 2005; 61: 3403
- 19 Joo JE, Pham VT, Tian YS, Chung YS, Oh CY, Lee KY, Ham WH. Org. Biomol. Chem. 2008; 6: 1498
- 20 Dhavale DD, Saha NN, Desai VN. J. Org. Chem. 1997; 62: 7482
- 21 Tsimilaza A, Tite T, Boutefnouchet S, Lallemand MC, Tillequin F, Husson HP. Tetrahedron: Asymmetry 2007; 18: 1585
- 22 Saksena AK, Lovey RG, Girijavallabhan VM, Ganguly AK, Mcphail AT. J. Org. Chem. 1986; 51: 5024