New, efficient, and high-yielding asymmetric synthesis of (4S,5S)-cytoxazone

Synthetic Communications

Volumn 42, Issue 17, 2012, Pages 2624-2631

  Babu, Kollapudi Chandra ^a,b   Reddy, Rapolu Naveen ^a   Rao, Salluri Yellamanda ^a   Venkateshwarlu, Palnati ^a   Madhusudhan, Gutta ^a  

^a Inogent Laboratories ^*  (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

(4R5R) cytoxazone; (4S5S) cytoxazone; (R) glyceraldehyde acetonide; Chiral N sulfinimine; Stereoselective 1,2 addition

Indexed keywords

BROMINE DERIVATIVE; CYTOXAZONE; EPICHLOROHYDRIN; GLYCERALDEHYDE; IMMUNOMODULATING AGENT; MAGNESIUM DERIVATIVE; SULFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBONYLATION; CHIRALITY; DRUG STRUCTURE; MELTING POINT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84861970811     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.563450     Document Type: Article

References (25)

1. Kakeya, H.; Morishita, M.; Koshino, H.; Morita, T.; Kobayashi, K.; Osada, H. Cytoxazone: A novel cytokine modulator containing a 2-oxazolidinone ring produced by streptomyces sp. J. Org. Chem. 1999, 64, 1052.
2. Kakeya, H.; Morishita, M.; Kobinata, K.; Osono, M.; Ishizuka, M.; Osada, H. Isolation and biological activity of a novel cytokine modulator, cytoxazone. J. Antibiot. 1999, 51, 1126.
3. Hamersak, Z.; Ljubovic, E.; Mercep, M.; Mesic, M.; Sunjic, V. Chemoenzymatic synthesis of all four cytoxazone stereoisomers. Synthesis 2001, 13, 1989.
4. Miyata, O.; Asai, H.; Naito, T. A Concise synthesis of (-)-cytoxazone and its stereoisomers via imino 1,2-wittig rearrangement. Synlett 1999, 12, 1915
5. Madhan, A.; Ravi Kumar, A.; Venkateswara Rao, B. Stereoselective synthesis of (-)-cytoxazone. Tetrahedron: Asymmetry 2001, 12, 2009.
6. Sakamoto, Y.; Shiraishi, A.; Seonhee, J.; Nakata, T. Stereoselective syntheses of cytoxazone, a novel cytokine modulator, and its stereoisomers. Tetrahedron Lett. 1999, 40, 4203.
7. Seki, M.; Mori, K. Synthesis of (-)-cytoxazone, a novel cytokine modulator isolated from Streptomyces sp. Eur. J. Org. Chem. 1999, 0, 2965.
8. Milicevic, S.; Matovic, R.; Saicic, R. N. Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone. Tetrahedron Lett. 2004, 45, 955.
9. Carter, P. H.; LaPorte, J. R.; Scherle, P. A.; Decicco, C. P. A new synthesis of cytoxazone and its diastereomers provides key initial SAR information. Bioorg. Med. Chem. Lett. 2003, 13, 1237
10. (a) Miyata, O.; Koizumi, T.; Ninomiya, I.; Naito, T. New imino-wittig rearrangement of benzyl and allyl hydroximates. J. Org. Chem. 1996, 61, 9078;
11. (b) Miyata, O.; Iba, R.; Hashimoto, J.; Naito, T. A convenient route to the furopyran core of dysiherbaine. Org. Biomol. Chem. 2003, 1, 772;
12. (c) Miyata, O.; Koizumi, T.; Asai, H.; Iba, R.; Naito, T. Imino 1,2-wittig rearrangement of hydroximates and its application to synthesis of cytoxazone. Tetrahedron 2004, 60, 3893-3914;
13. (d) Miyata, O.; Hashimoto, J.; Iba, R.; Naito, T. Preparation of optically active α -hydroxy oxime ether by diastereoselective imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of (+)-cytoxazone. Tetrahedron Lett. 2005, 46, 4015.
14. Chandra Babu, K.; Raman, V.; Srinivas, K. S. V.; Satish, N.; Madhusudhan, G.; Mukkanti, K. Asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5- carboxylic acid using 1,2-addition of PhMgBr to N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA. Tetrahedron: Asymmetry 2010, 21, 2619-2624.
15. (a) Evans, J. W.; Ellman, J. A. Stereoselective synthesis of 1,2-disubstituted β-amino alcohols by nucleophilic addition to N-tert-butanesulfinyl α-alkoxyaldimines. J. Org. Chem. 2003, 68, 9948-9957;
16. (b) Morton, D.; Stockman, R. A. Chiral non-racemic sulfinimines: Versatile reagents for asymmetric synthesis. Tetrahedron. 2006, 62, 8869-8905. (Pubitemid 44218983)
17. (a) Davies, S. G.; Hughes, D. G.; Nicholson, R. L.; Smith, A. D.; Wright, A. Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone. J. Org. Biomol. Chem. 2004, 2, 1549;
18. (b) Paraskar, A. S.; Sudalai, A. Enantioselective synthesis of (L)-cytoxazone and (+)-epicytoxazone, novel cytokine modulators via Sharpless asymmetric epoxidation and L-proline-catalyzed Mannich reaction. Tetrahedron 2006, 62, 5756;
19. 4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: A short route to (-)-cytoxazone and droxidopa. Tetrahedron Lett. 2007, 48, 1375;
20. (d) Bunnage, M. E.; Chernega, A. N.; Davies, S. G.; Goodwin, C. J. Asymmetric synthesis of p-amino-a-hydroxy acids via diastereoselective hydroxylation of homochiral p-amino enolates. J. Chem. Soc., Perkin Trans. 1994, 1 2373;
21. (e) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. Asymmetric synthesis of allophenylnorstatine. Synlett 1993, 0, 731;
22. (f) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Ichihara, O. An expeditious asymmetric synthesis of allophenylnorstatine. Tetrahedron 1994, 50, 3975;
23. (g) Bashiardes, G.; Bodwell, G. J.; Davies, S. G. Asymmetric synthesis of (-)-actinonin and (-)-epi-actinonin. J. Chem. Soc., Perkin Trans. 1993, 1 459;
24. (h) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. Asymmetric synthesis of the taxol and taxotere C-13 side chains. J. Chem. Soc., Perkin Trans. 1994, 1 2385.
25. Morton, D.; Stockman, R. A. Chiral non-racemic sulfinimines: Versatile reagents for asymmetric synthesis. Tetrahedron 2006, 62, 8869-8905, and references cited therein. (Pubitemid 44218983)