A chemoenzymatic asymmetric synthesis of the hydroxy acid segment of schulzeines B and C

Tetrahedron Asymmetry

Volumn 21, Issue 1, 2010, Pages 27-32

  Biswas, Sucheta ^a   Chattopadhyay, Subrata ^a   Sharma, Anubha ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 CYCLOHEXYLIDENEDIOXYTRIDECAN 3 OL; 12 ACETOXYTETRADEC 13 EN 1 OL; 12 ACETOXYTETRADECAN 13 ENAL; 12 TERT BUTYLDIPHENYLSILYLOXYDODECAN 1 OL; 12 TERT BUTYLDIPHENYLSILYLOXYDODECANAL; 14 TERT BUTYLDIPHENYLSILYLOXYTETRADEC 1 EN 3 OL; 3 ACETOXY 14 TERT BUTYLDIPHENYLSILYLOXYTETRADEC 1 ENE; 3 BENZYLOXY 1,2 CYCLOHEXYLIDENEDIOXYTRIDECANE; 3 BENZYLOXY 1,2 EPOXYTRIDECANE; 3 BENZYLOXYTRIDECANE 1,2 DIOL; 4 BENZYLOXYTETRADEC 1 EN 3 OL; ALCOHOL DERIVATIVE; EPOXIDE; ETHYL 14 ACETOXY 17 HYDROXY 18 BENZYLOXYOCTACOSA DIENOATE; ETHYL 14 ACETOXY 17,18 DIHYDROXYOCTACOSANOATE; ETHYL 14 ACETOXYHEXADECA 2E,15 DIENOATE; ETHYL 14,17 18 TRIHYDROXYOCTACOSANOATE; GLYCERALDEHYDE; HYDROXYACID; SCHULZEINE B; SCHULZEINE C; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 76049092856     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.12.020     Document Type: Article

References (56)

1. Takada K., Uehara T., Nakao Y., Matsunaga S., Van Soest R.W.M., and Fusetani N. J. Am. Chem. Soc. 126 (2004) 187-193
2. Burgoyne D.L., Miao S., Pathirana C., Andersen R.J., Ayer W.A., Singer P.P., Kokke W.C.M.C., and Ross D.M. Can. J. Chem. 69 (1991) 20-27
3. Ohba M., Nishimura Y., Kato M., and Fujii T. Tetrahedron 55 (1999) 4999-5016
4. Nakao Y., Maki T., Matsunaga S., Van Soest R.W.M., and Fusetani N. Tetrahedron 56 (2000) 8977-8987
5. Bowen E.G., and Wardrop D.J. J. Am. Chem. Soc. 131 (2009) 6062-6063
6. For a review of glycosidase inhibitors, see:. Jung M., Park M., Lee H.C., Kang Y.-H., Kang E.S., and Kim S.K. Curr. Med. Chem. 13 (2006) 1203-1218
7. Braun C., Brayer G.D., and Withers S.G. J. Biol. Chem. 270 (1995) 26778-26781
8. Mehta A., Zitzmann N., Rudd P.M., Block T.M., and Dwek R.A. FEBS Lett. 430 (1998) 17-22
9. Dwek R.A., Butters T.D., Platt F.M., and Zitzmann N. Nat. Rev. Drug Discovery 1 (2002) 65-75
10. Kuntiyong P., Akkarasamiyo S., and Eksinitkun G. Chem. Lett. 35 (2006) 1008-1009
11. Gurjar M.K., Pramanik C., Bhattasali D., Ramana C.V., and Mohapatra D.K. J. Org. Chem. 72 (2007) 6591-6594
12. Liu G., and Romo D. Org. Lett. 11 (2009) 1143-1146
13. Vyavahare V.P., Chakraborty C., Maity B., Chattopadhyay S., Puranik V.G., and Dhavale D.D. J. Med. Chem. 50 (2007) 5519-5523
14. Maity B., Banerjee D., Bandyopadhyay S.K., and Chattopadhyay S. Int. Immunopharm. 9 (2009) 491-498
15. Nakao Y., Maki T., Matsunaga S., van Soest R.W.M., and Fusetani N. J. Nat. Prod. 67 (2004) 1346-1350
16. Nakao Y., Maki T., Matsunaga S., van Soest R.W.M., and Fusetani N. Tetrahedron 56 (2000) 8977-8987
17. Turner W.B., and Aldridge D.C. Fungal Metabolites II (1983), Academic Press, London
18. Gardner H.W. J. Lipid Res. 11 (1970) 311-321
19. Kawagishi H., Ando M., Micno T., Yokota H., and Konishi S. Agric. Biol. Chem. 54 (1990) 1329-1331
20. Kuga H., Ejima A., Mitui I., Sato K., Ishihara N., Fukunda K., Saito F., and Uenaki K. Biosci. Biotech. Biochem. 57 (1993) 1020-1021
21. Simon B., Anke T., and Sterner O. Phytochemistry 36 (1994) 815-816
22. Nagai T., Kiyohara H., Munakata K., Shirahata T., Sunazuka T., Harigaya Y., and Yamada H. Int. Immunopharm. 2 (2002) 1183-1193
23. Nicolaou K.C., Vourloumis D., Winssinger N., and Baran P.S. Angew. Chem., Int. Ed. 39 (2000) 44-122
24. Corey E.J., and Guzman-Perez A. Angew. Chem., Int. Ed. 37 (1998) 388-401
25. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), Wiley, New York
26. Salaskar A., Mayekar N.V., Sharma A., Chattopadhyay A., Nayak S.K., and Chattopadhyay S. Synthesis (2005) 2777-2781
27. Salaskar A., Sharma A., and Chattopadhyay S. Tetrahedron: Asymmetry 17 (2006) 325-329
28. Roy S., Sharma A., Chattopadhyay N., and Chattopadhyay S. Tetrahedron Lett. 47 (2006) 7067-7069
29. Roy S., Sharma A., Dhotare B., Vichare P., Chattopadhyay A., and Chattopadhyay S. Synthesis (2007) 1082-1090
30. Sharma A., Gamre S., and Chattopadhyay S. Tetrahedron Lett. 48 (2007) 633-634
31. Sharma A., Gamre S., and Chattopadhyay S. Tetrahedron Lett. 48 (2007) 3705-3707
32. Sharma A., Gamre S., Roy S., Goswami D., Chattopadhyay A., and Chattopadhyay S. Tetrahedron Lett. 49 (2008) 3902-3905
33. Sharma A., Das P., and Chattopadhyay S. Tetrahedron: Asymmetry 19 (2008) 2167-2170
34. Sharma A., and Chattopadhyay S. J. Org. Chem. 63 (1998) 6128-6131
35. Sharma A., and Chattopadhyay S. J. Org. Chem. 64 (1999) 8059-8062
36. Sharma A., Gamre S., and Chattopadhyay S. Lett. Org. Chem. 2 (2005) 547-549
37. Kumar A.N., Bhatt S., and Chattopadhyay S. Tetrahedron: Asymmetry 20 (2009) 205-209
38. Armstrong S.K. J. Chem. Soc. Perkin Trans. 1 (1998) 371-388;
39. Schrock R.R. Tetrahedron 55 (1999) 8141-8153
40. Fürstner A. Angew. Chem. Int. Ed 39 (2000) 3012-3043
41. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18-29
42. Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 58-71
43. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
44. Sharma A., Gamre S., and Chattopadhyay S. Tetrahedron: Asymmetry 20 (2009) 1164-1167
45. Sharma A., Mahato S., and Chattopadhyay S. Tetrahedron Lett. 50 (2009) 4986-4988
46. Reetz M.T. Curr. Opin. Chem. Biol. 6 (2002) 145-150
47. Faber K. Biotransformations in Organic Chemistry. 5th ed. (2004), Springer, Heidelberg, Germany
48. Bornscheuer U.T., and Kazlauskas R.J. Hydrolases in Organic Synthesis. 2nd ed. (2005), Wiley-VCH, Weinheim, Germany
49. Gotor-Fernández V., Busto E., and Gotor V. Adv. Synth. Catal. (2006) 797-812
50. Ohtani T., Nakatsukasa H., Kamezawa M., Tachibana H., and Naoshima Y. J. Mol. Catal. B: Enzym. 4 (1998) 53-60
51. Fuji M., Fukumura M., Hory Y., Hirai Y., Akita H., Nakamura K., Toriizuka K., and Ida Y. Tetrahedron: Asymmetry 17 (2006) 2292-2298
52. Felluga F., Forzato C., Ghelfi F., Nitti P., Pitacco G., Pagnoni U.M., and Roncaglia F. Tetrahedron: Asymmetry 18 (2007) 527-536
53. Dale J.A., and Mosher S.H. J. Am. Chem. Soc. 95 (1973) 512-519
54. Che C., Zhang Z.-N., Huang G.-L., and Wang X.-X. Chin. J. Org. Chem. 24 (2004) 1281-1283
55. Dhotare B., Salaskar A., and Chattopadhyay A. Synthesis (2003) 2571-2575
56. Gravier-Pelletier C., Le Merrer Y., and Depezay J.-C. Tetrahedron 51 (1995) 1663-1674