Stereoselective total synthesis of putaminoxin

Synthesis

Volumn 44, Issue 4, 2012, Pages 585-590

  Yadav, Jhillu Singh ^a,b   Raju, Ande ^a,c   Ravindar, Kontham ^a   Reddy, Basi V Subba ^a   Khazim Al Ghamdi, Ahmad Al ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c UNIVERSITY OF HYDERABAD   (India)

Author keywords

Birch reduction; Jacobsens kinetic resolution; macrolide; necrotic leaf disease; Sharpless asymmetric epoxidation; Yamaguchi lactonization

Indexed keywords

ASYMMETRIC EPOXIDATION; BIRCH REDUCTION; JACOBSENS KINETIC RESOLUTION; LACTONIZATION; MACROLIDES; NECROTIC LEAF;

METABOLITES;

STEREOSELECTIVITY;

12 (BENZYLOXY) 8 (TERT BUTYLDIMETHYLSILOXY)DODEC 6 YN 4 OL; 2 [4 (BENZYLOXY)BUTYL] 3 (CHLOROMETHYL)OXIRANE; 2 PROPYLOXIRANE; 5 (BENZYLOXY)PENTAN 1 OL; 5 (TERT BUTYLDIMETHYLSILOXY) 9 HYDROXYDODEC 6 ENOIC ACID; 5 (TERT BUTYLDIMETHYLSILOXY)DODEC 6 ENE 1,9 DIOL; 6 (TERT BUTYLDIMETHYLSILOXY) 10 PROPYL 3,4,5,6,9,10 HEXAHYDRO 2H OXECIN 2 ONE; 6 HYDROXY 10 PROPYL 3,4,5,6,9,10 HEXAHYDRO 2H OXECIN 2 ONE; 7 (BENZYLOXY)HEPT 1 YN 3 OL; 7 (BENZYLOXY)HEPT 2 EN 1 OL; [3 [4 (BENZYLOXY)BUTYL]OXIRAN 2 YL]METHANOL; [7 (BENZYLOXY)HEPT 1 YN 3 YLOXY](TERT BUTYL)DIMETHYLSILANE; ALCOHOL; ALKYNE; ETHYL 7 (BENZYLOXY)HEPT 2 ENOIC ACID; ETHYLENE OXIDE; HERBICIDE; HYDROXYACID; MACROLIDE; PUTAMINOXIN; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; BIRCH REDUCTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ISOLATION PROCEDURE; OXIDATION; SHARPLESS EPOXIDATION; STEREOCHEMISTRY;

EID: 84857030724     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290156     Document Type: Article

References (33)

1. Evidente A, Lanzetta R, Capasso R, Andolfi A, Bottalico A, Vurro M, Zonno M C., Phytochemistry 1995 40 1637
2. Fuschser J, Zeeck A, Liebigs Ann./Recl. 1997 87
3. Sabitha G, Padmaja P, Reddy P N., Yadav J S., Tetrahedron Lett. 2010 51 6166
4. Evidente A, Capasso R, Andolfi A, Vurro M, Zonno M C., Nat. Toxins 1998 6 183
5. Sabitha G, Yadagiri K, Swapna R, Yadav J S., Tetrahedron Lett. 2009 50 5417
6. Kamal A, Reddy P V., Balakrishna M, Prabhakar S, Lett. Org. Chem. 2011 8 143
7. Smith A B. III., Lin Q, Doughty V A., Zhuang L, McBriar M D., Kerns J K., Boldi A M., Murase N, Moser W H., Brook C S., Bennett C S., Nakayama K, Sobukawa M, Lee Trout R E., Tetrahedron 2009 65 6470
8. Osterkamp F, Ziemer B, Koert U, Wiesner M, Raddatz P, Goodman S L., Chem. Eur. J. 2000 6 666
9. Pihko P M., Aho J E., Org. Lett. 2004 6 3849
10. Liu J, Yang J H., Ko C, Hsung R P., Tetrahedron Lett. 2006 47 6121
11. Yadav J S., Sreenivas M, Reddy A S., Reddy B V. S., J. Org. Chem. 2010 75 8307
12. Perepogu A K., Raman D, Murty U S. N., Rao V J., Bioorg. Chem. 2009 37 46
13. Finn M G., Sharpless K B., In Asymmetric Synthesis Vol. 5 Morrison J D. Acadamic Press New York 1985 Chap. 8 247
14. Pfenninger A, Synthesis 1986 89
15. Katsuki T, Sharpless K B., J. Am. Chem. Soc. 1980 102 5974
16. Gao Y, Hanson R M., Klunder J M., Ko S Y., Masamune H, Sharpless K B., J. Am. Chem. Soc. 1987 109 5765
17. Yadav J S., Reddy Ch S., Org. Lett. 2009 11 1705
18. Yadav J S., Deshpande P K., Sharma G V. M., Tetrahedron 1990 46 7033
19. Braun M G., Vincent A, Boumediene M, Prunet J, J. Org. Chem. 2011 76 4921
20. Florence G J., Cadou R F., Tetrahedron Lett. 2010 51 5761
21. Tokunaga M, Larrow J F., Kakiuchi F, Jacobsen E N., Science 1997 277 936
22. Kretschmer M, Menche D, Synlett 2010 2989
23. Van de Weghe P, Bourg S, Eustache S, Tetrahedron 2003 59 7365
24. Burova S A., McDonald F E., J. Am. Chem. Soc. 2002 124 8188
25. Yadav J S., Sipak J, Dutta S K., Kunwar A C., Tetrahedron Lett. 2007 48 5335
26. Naidu V S., Gupta P, Kumar P, Tetrahedron 2007 63 7624
27. Hansen M T., Florence G J., Lugo-Mas P, Chen J, Abrams J C., Forsyth C J., Tetrahedron Lett. 2003 44 57
28. Bal B S., Childers W E., Pinnick H W. Jr., Tetrahedron 1981 37 2091
29. Yadav J S., Thrimurthulu N, Venkatesh M, Rao K V. R., Prasad A R., Reddy B V. S., Synthesis 2010 73
30. Shiina I, Fujisawa H, Ishii T, Fukuda Y, Heterocycles 2000 52 1105
31. Sabitha G, Reddy R T., Ramesh M, Srinivas C, Yadav J S., Bull. Chem. Soc. Jpn. 2011 84 229
32. Kaliappan K P., Si D, Synlett 2009 2441
33. Srihari P, Kumaraswamy B, Somaiah K, Yadav J S., Synthesis 2010 1039