Asymmetric synthesis of palitantin by an enzymatic and organocatalytic approach

Tetrahedron Asymmetry

Volumn 20, Issue 5, 2009, Pages 610-615

  Mahapatra, Tridib ^a   Nanda, Samik ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FREQUENTIN; KETOL; PALITANTIN; POLYKETIDE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOCATALYST; CATALYSIS; DIHYDROXYLATION; FUNGUS; METHYLATION; PENICILLIUM FREQUENTANS; PENICILLIUM PALITANST; PRIORITY JOURNAL; SHARPLESS ASYMMETRIC DIHYDROXYLATION; STEREOCHEMISTRY;

EID: 65349151885     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.02.055     Document Type: Article

References (37)

1. Birkinshaw J.H., and Raistvick H. Biochem. J. 30 (1936) 801
2. Birkinshaw J.H. Biochem. J. 51 (1952) 271
3. Bowden K., Lythgoe B., and Marsden D.J.S. J. Chem. Soc. (1959) 1662
4. Curtis P.J., Hemming G.H., and Smith W.K. Nature 167 (1951) 557
5. Sigg H.P. Helv. Chim. Acta 46 (1963) 1061
6. Hong B.C., Wu M.-F., Tseng H.-C., Huang G.-F., Su C.-F., and Liao J.-H. J. Org. Chem. 72 (2007) 8459
7. Hareau G., Koiwa M., Hanazawa T., and Sato F. Tetrahedron Lett. 40 (1999) 7493
8. Deruyttere X., Dumortier L., Van der Eycken J., and Vandewalle M. Synlett (1992) 51
9. Hanessian S., Sakito Y., Dhanoa D., and Baptistella L. Tetrahedron 45 (1989) 6623
10. Barral K., Courcambeck J., Pepe G., Balzarini J., Neyts J., De Clercg E., and Camplo M. J. Med. Chem. 48 (2005) 450
11. Hatcher M.A., Peleg S., Dolan P., Kensler T.W., Sarjeant A., and Posner G.H. Bioorg. Med. Chem. 13 (2005) 3964
12. Yu S.-H., and Chung S.-K. Tetrahedron: Asymmetry 15 (2004) 581
13. Smith A.B., Hale K.J., Laakso L.M., Chen K., and Riera A. Tetrahedron Lett. 30 (1989) 6963
14. Linde R.G., Egbertson M., Coleman R.S., Jones A.B., and Danishefsky S.J. J. Org. Chem. 55 (1990) 2771
15. Hodgson D.M., Gibbs A.R., and Drew M.G.B. Perkin Trans. 1 (1999) 3579
16. Miyaoka H., Sagawa S., Inoue T., Nagaoka H., and Yamada Y. Chem. Pharm. Bull. 42 (1994) 405
17. Trost B.M., Richardson J., and Yong K. J. Am. Chem. Soc. 128 (2006) 2540
18. The enantioselectivity was measured by chiral HPLC (OJ-H, hexane-2-propanol/9:1) measurement of the benzoate derivative of (R) and (S)-1.
19. Peng J., and Clive D.L.J. J. Org. Chem. 74 (2009) 513
20. Tietze L.F., Eicher T., Diederichsen U., and Speicher A. Reactions and Syntheses (2007), Springer, Weinheim 211
21. Todoroki Y., and Hirai N. Tetrahedron 56 (2000) 8095
22. Kitamura M., Isobe M., Ichikawa Y., and Goto T. J. Am. Chem. Soc. 106 (1984) 3252
23. 2, after usual workup we treat the reaction mixture (mixture of compound 5 with acetonide deprotected diol) with 2,2-DMP and PPTS to yield compound 5
24. Hanessian S., and Lavallee P. Can. J. Chem. 53 (1975) 2975
25. Dei S., Bellucci C., Buccioni M., Ferrarono M., Gualtieri F., Guandalini L., Manetti D., Matucci R., Romanelli M.N., Scapecchi S., and Deodori E. Biorg. Med. Chem. 11 (2003) 3153
26. Watanabe Y., Lida H., and Kibayashi C. J. Org. Chem. 54 (1989) 4088
27. Coldham L., Crapnell K.M., Moseley J.D., and Rabot R. Perkin Trans. 1 (2001) 1758
28. Deguest G., Bischoff L., Fruit C., and Marsais F. Org. Lett. 9 (2007) 1165
29. Bach T. Angew. Chem., Int. Ed. Engl. 33 (1994) 417
30. Groger H., Vogl E.M., and Shibasaki M. Chem. Eur. J. 4 (1998) 1137
31. Nelson S.G. Tetrahedron: Asymmetry 9 (1998) 357
32. Machajewski T.D. Angew. Chem., Int. Ed. Engl. 39 (2000) 1352
33. List B. Synlett (2001) 1675
34. List B. Tetrahedron 58 (2002) 5573
35. List B. Acc. Chem. Res. 37 (2004) 548
36. Movassaghi M., and Jacobsen E.N. Science 298 (2002) 1904
37. Casas J., Sunden H., and Cordova A. Tetrahedron Lett. 45 (2004) 6117