Stereoselective synthesis of (+)-nephrosteranic acid by ring-closing metathesis and its biological evaluation

Synthetic Communications

Volumn 40, Issue 5, 2010, Pages 686-696

  Perepogu, Arun Kumar ^a   Raman, D ^b   Murty, U S N ^b   Rao, Vaidya Jayathirtha ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Antimicrobial activity; Chemoselective reduction; Gilman 1,4 addition; Paraconic acids; Ring closing metathesis; Sharpless asymmetric epoxidation

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; GAMMA BUTYROLACTONE; LAURYL ALCOHOL; NEPHROSTERANIC ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL STRAIN; CELL STRAIN U937; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; FUNGAL STRAIN; HUMAN; HUMAN CELL; LEUKEMIA CELL; LYMPHOMA CELL LINE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; RING CLOSING METATHESIS; SHARPLESS EPOXIDATION; STEREOCHEMISTRY;

EID: 76349103731     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903011337     Document Type: Article

References (37)

1. Jacobi, P. A.; Herradura, P. Enantioselective synthesis of (+) and (\-)-phaseolinic acid. Tetrahedron Lett. 1996, 37, 8297-8300.
2. (a) Maier, M. S.; Marimon, D. I. G.; Stortz, C. A.; Adler, M. T. A revised structure for (\-)-dihydropertusaric acid, a c-butyrolactone acid from the lichen Punctelia microsticta. J. Nat. Prod. 1999, 62, 1565-1567;
3. (b) Lee, S. C; Brown, G. D. Tribenzylbutyrolactones and dibenzyldiphenyl-4,5,6,7-tetrahydrobenzofuranones from Kyrtuthrix maculans. J. Nat. Prod. 1998, 61, 29-33.
4. (a) Loh, T. P.; Lye, P. L. Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: A short synthesis of (\-)-roccellaric acid. Tetrahedron Lett. 2001, 41, 561-563;
5. (b) Mandal, P. K.; Roy, S. C. Total synthesis of (±)- dihydroprotolichesterinic acid and formal synthesis of (±)-roccellaric acid by radical cyclisation of an epoxide using a transition-metal radical source. Tetrahedron 1999, 55, 11395-11398;
6. (c) Lertvorachon, J.; Meepowpan, P.; Thebtaranonth, Y. An aldol-bislactonization route to a-methylene bis-c-butyrolactones. Tetrahedron 1998, 54, 14341-14348;
7. (d) Mandal, P. K.; Maiti, G.; Roy, S. C. Stereoselective synthesis of polysubstituted tetrahydrofurans by radical cycliza-tion of epoxides using a transition-metal radical source: Application to the total synthesis of (±)-methylenolactocin and (±)-protolichesteranic acid. J. Org. Chem. 1998, 63, 2829-2834.
8. (a) Masaki, Y.; Arasaki, H.; Itoh, A. Enantiodivergent synthesis of both enantiomeric forms of substituted paraconic acids starting from mannitol as a chiral pool. Tetrahedron Lett. 1999, 40, 4829-4832;
9. (b) Mulzer, J.; Salimi, N.; Hartl, H. First asymmetric synthesis of (+) and (\-)-roccellaric acid and dihydroprotolichesterinic acid. Tetrahedron: Asymmetry 1993, 4, 457-471.
10. (a) Bella, V.; Margarita, V.; Orlando, C; Orsini, M.; Parlanti, L.; Piancatelli, G. a-Cyano-c-lactones by photoinduced electron-transfer-catalyzed oxidation of a-hydroxyalkylsi-lanes in the prescence of a-cyano acrylates. Tetrahedron Lett. 2000, 41, 561-565;
11. (b) Sibi, M. P.; Ji, J. Regio-and stereocontrolled conjugate radical addition to a desymmetrized fumarate derivative: An efficient synthesis of (\-)-nephrosteranic acid and (\-)-roccellaric acid. Angew. Chem., Int. Ed. Engl. 1997, 36, 274-276;
12. Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. Synthesis and absolute stereochemistry of (\-)-protolichesterinic acid, antitumor antibiotic lactone from Cetraria islandica. J. Org. Chem. 1993, 58, 7537-7541.
13. (a) Chandrasekharam, M.; Liu, R. S. An aldol-bislactonization route to cx-methylene bis-y-butyrolactones: Synthesis of natural cx-methylene butyrolactones via tungsten-7i-allyl complexes: Total synthesis of (\-)-methylenolactocin. J. Org. Chem. 1998, 63, 9122-9124;
14. (b) Vaupel, A.; Knochel, P. Stereoselective synthesis of heterocyclic zinc reagents via a nickel-catalysed radical cyclization. J. Org. Chem. 1996, 61, 5743-5753.
15. Barros, M. T.; Maycock, C. D.; Venturia, M. R. Aldol reactions of diaxanes derived from tartaric acid: A total synthesis of nephrosteranic acid. Org. Lett. 2003, 5, 4097-4099.
16. (a) Narender, P.; Gangadasu, B.; Ramesh, C; China Raju, B.; Rao, V. J. Facile and selective synthesis of chloromethylpyridines and chloropyridines using diphosgene/triphos-gene. Synth. Commun. 2004, 34, 1097-1103;
17. (b) Gangadasu, B.; Narender, P.; Bharath Kumar, S.; Ravinder, M.; Ananda Rao, B.; Ramesh, C; China Raju, B.; Rao, V. J. Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction. Tetrahedron 2006, 62, 8398-8403;
18. (c) Narender, P.; Srinivas, U.; Gangadasu, B.; Biswas, S.; Rao, V. J. Anti-malarial activity of Baylis-Hillman adducts from substituted 2-chloronicotinalde-hydes. Bioorg. Med. Chem. Lett. 2005, 15, 5378-5381;
19. (d) Srinivas, K.; Srinivas, U.; Bhanuprakash, K.; Harakishore, K.; Murthy, U. S. N; Rao, V. J. Synthesis and antibacterial activity of various substituted s-triazines. Eur. J. Med. Chem. 2006, 41, 1240-1246;
20. (e) Srinivasa Rao, M.; Murty, U. S. N; Gangadasu, B.; China Raju, B.; Ramesh, C; Bharat Kumar, S.; Rao, V. J. Larvicidal efficacy of neonicotinoid classes of compounds on Culexquinquefasciatus. J. Entomol. 2008, 5, 45-50.
21. Hon, Y. S.; Lu, L.; Li, S. Y. The reaction of ozonides from mono-substituted alkenes with stabilized phosphorus ylides. J. Chem. Soc, Chem. Commun. 1990, 1627-1628.
22. Park, S. U.; Chung, S. K.; Newcomb, M. Evidence supporting two-electron nucleophilic displacement in reactions of unhindered alkyl bromides and iodides with boron and aluminum hydride reducing agents. J. Org. Chem. 1987, 52, 3275-3278.
23. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, Y. S.; Masamune, H.; Sharpless, B. K. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization. J. Am. Chem. Soc. 1987, 109, 5765-5780.
24. Liu, Z.; Lan, J.; Li, Y. Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: First total synthesis of (\-)-4-O-(6'-hydroxy- 7'(9')-dehyro-6',7'-dihydrogeranyl)coniferol. Tetrahedron: Asymmetry 1998, 9, 3755-3762.
25. Ghosh, K. A.; Liu, C A stereoselective synthesis of (\-)- tetrahydrolipstatin. Chem. Commun. 1999, 1743-1744.
26. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Ring-closing metathesis and related processes in organic synthesis. Acc. Chem. Res. 1995, 28, 446-452;
27. (b) Schuster, M.; Blechert, S. Olefin metathesis in organic chemistry. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056;
28. (c) Bassetti, M.; Annibale, A. D.; Fanfoni, A.; Minissi, F. Synthesis of cx,P-unsaturated 4,5-disubstituted y-lactones via ring-closing metathesis catalyzed by the first-generation Grubb's catalyst. Org Lett. 2005, 7, 1805-1808.
29. Harding, E. K; Clement, A. B.; Moreno, L.; Katalinic, J. P. Synthesis of some polyfunc-tionalized bicyclo[3.3.1]nonane-2,9-diones and bicyclo[4.3.1]decane-2,10-diones. J. Org. Chem. 1981, 46, 940-948.
30. Schollkopf, U.; Paust, J.; Patsch, M. R. Org. Synth., Coll. Vol.V, 1973, 859.
31. Marshall, J. A.; Brady, S. F. The total synthesis of (±)-hinesol. J. Org. Chem. 1970, 35, 4068-4077.
32. House, H. O.; Thompson, H. W. The chemistry of carbanions IV: The stereochemistry of conjugated Grignard addition. J. Org. Chem. 1963, 28, 360-365.
33. Seki, M.; Shimizu, T.; Matsumoto, K. Stereoselective synthesis of P-benzyl-cx-alkyl-P-amino acids from L-aspartic acid. J. Org. Chem. 2000, 65, 1298-1304.
34. Mulzer, J.; Kattner, L.; Strecker, R. A.; Schroder, C.; Buschmann, J.; Lehmann, C.; Luger, P.; Felkin, A. Highly selective Hiyama additions of chiral allylic bromides to aldehydes: Application to the first synthesis of nephromopsinic acid and its enantiomer. J. Am. Chem. Soc. 1991, 113, 4218-4229.
35. National Committee for Clinical Laboratory Standard. Reference Method for Broth Dilution Antifungal Susceptibility; National Committee for Clinical Laboratory Standards: Wayne, PA 1997(a);
36. National Committee for Clinical Laboratory Standard. Reference Method for Broth Dilution Antifungal Susceptibility; National Committee for Clinical Laboratory Standard: Wayne, PA 1998(b).
37. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55.