Total synthesis of xestodecalactone c from L-malic acid

Synthesis

Volumn , Issue 18, 2009, Pages 3157-3161

  Yadav, J S ^a   Rao, Y Gopala ^a   Ravindar, K ^a   Reddy, B V Subba ^a   Narsaiah, A V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Barbier allylation; Intramolecular Friedel Crafts acylation; Stereoselective reduction; Xestodecalactone C

Indexed keywords

ALLYLATIONS; ASYMMETRIC REDUCTION; BARBIER ALLYLATION; FRIEDEL-CRAFTS ACYLATION; INTRAMOLECULAR FRIEDEL-CRAFTS ACYLATION; L-MALIC ACID; MACROLIDES; STEREO-SELECTIVE; STEREOSELECTIVE REDUCTION; SYNTHETIC SEQUENCE; TOTAL SYNTHESIS; XESTODECALACTONE C;

ACYLATION;

STEREOSELECTIVITY;

ANTIINFECTIVE AGENT; MACROLIDE; MALIC ACID; NATURAL PRODUCT; UNCLASSIFIED DRUG; XESTODECALACTONE A; XESTODECALACTONE B; XESTODECALACTONE C;

ACYLATION; ALLYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 70449367309     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216938     Document Type: Article

References (20)

1. Edrada, R. A.; Heubes, M.; Brauers, G.; Wray, V.; Berg, A.; Gräfe, U.; Wohlfarth, M.; Mühlbacher, J.; Schaumann, K.; Sudarsono; Bringmann, G.; Proksch, P. J. Nat. Prod. 2002, 65, 1598.
2. Kinoshita, K.; Sasaki, T.; Awata, M.; Takada, M.; Yaginuma, S. J. Antibiot. 1997, 50, 961.
3. Musgrave, O. C. J. Chem. Soc. 1956, 4301.
4. Lai, S.; Shizuri, Y.; Yamamura, S.; Kawai, K.; Terada, Y.; Furukuwa, H. Tetrahedron Lett. 1989, 30, 2241.
5. Robeson, D. J.; Strobel, G. A.; Strange, R. N. J. Nat. Prod. 1985, 48, 139.
6. Ghisalberti, E. L.; Rowland, C. Y. J. Nat. Prod. 1993, 56, 2175.
7. Liang, Q.; Zhang, J.; Quan, W.; Sun, Y.; She, X.; Pan, X. J. Org. Chem. 2007, 72, 2694.
8. Bringmann, G.; Proksch, P.; Edrada, R. A.; Heubes, M.; Sudarsono; Gunther, E. US 2003,216,354, 2003.
9. Bringmann, G.; Lang, G.; Michel, M.; Heubes, M. Tetrahedron Lett. 2004, 45, 2829.
10. Yoshino, T.; Ng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 14185.
11. Yadav, J. S.; Thrimurtulu, N.; Uma Gayathri, K.; Subba Reddy, B. V.; Prasad, A. R. Tetrahedron Lett. 2008, 49, 6617.
12. Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Can. J. Chem. 1984, 62, 2146.
13. Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910.
14. Luche, J.-L.; Einhorn, C. J. Organomet. Chem. 1987, 322, 177.
15. Ghosh, A. K.; Lei, H. J. Org. Chem. 2002, 67, 8783.
16. Sabitha, G.; Sudhakar, K.; Mallikarjun Reddy, N.; Rajkumar, M.; Yadav, J. S. Tetrahedron Lett. 2005, 46, 6567.
17. Baker, P. M.; Bycroft, B. W.; Roberts, J. C. J. Chem. Soc. C 1967, 1913.
18. Bal, B. S.; Childers, W. E.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
19. Bracher, F.; Schulte, B. Liebigs Ann./Recl. 1997, 1979.
20. Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287.