Enantioselective synthesis of phomallenic acid C by In- and Pd-mediated anti-SN2′ coupling

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 6953-6958

  Kato, Tomoko ^a   Ishigami, Ken ^a   Akasaka, Kazuaki ^b   Watanabe, Hidenori ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SHOKEI GAKUIN UNIVERSITY   (Japan)

Author keywords

anti SN2 Coupling; Inhibitor of FAS II pathway; Ohrui Akasaka method; Organoindium; Phomallenic acid C

Indexed keywords

DIYNYLINDIUM; FATTY ACID SYNTHASE INHIBITOR; INDIUM; PALLADIUM; PHOMALLENIC ACID A; PHOMALLENIC ACID B; PHOMALLENIC ACID C; PROPARGYL MESYLATE; UNCLASSIFIED DRUG;

ANTI SN 2' COUPLING REACTION; ANTIBACTERIAL ACTIVITY; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHIRALITY; DRUG PURITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME INHIBITION; FATTY ACID SYNTHESIS; NONHUMAN; OHRUI AKASAKA METHOD; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION OPTIMIZATION;

BACTERIA (MICROORGANISMS);

EID: 67650547229     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.054     Document Type: Article

References (18)

1. Ondeyka J.G., Zink D.L., Young K., Painter R., Kodali S., Galgoci A., Collado J., Tormo J.R., Basilio A., Vicente F., Wang J., and Singh S.B. J. Nat. Prod. 69 (2006) 377-380
2. Zhang Y.-M., White S.W., and Rock C.O. J. Biol. Chem. 281 (2006) 17541-17544
3. Young K., Jayasuriya H., Ondeyka J.G., Herath K., Zhang C., Kodali S., Galgoci A., Painter R., Driver V.B., Yamamoto R., Silver L.L., Zheng Y., Ventura J.I., Sigmund J., Ha S., Basilio A., Vicente F., Tormo J.R., Pelaez F., Yongman P., Cully D., Barrett J.F., Schmatz D., Singh S.B., and Wang J. Antimicrob. Agents Chemother. (2006) 519-526
4. Lowe D. J. Chem. Soc., Chem. Commun. (1965) 411-413
5. Jian Y.-J., Tang C.-J., and Wu Y. J. Org. Chem. 72 (2007) 4851-4855
6. Elsevier C.J., Meijer J., Tadema G., Stehouwer P.M., Bos H.J.T., and Vermeer P. J. Org. Chem. 47 (1982) 2194-2196
7. Ishigami K., Kato T., Akasaka K., and Watanabe H. Tetrahedron Lett. 49 (2008) 5077-5079
8. Yoshida M., Al-Amin M., and Shishido K. Synthesis (2008) 1099-1105
9. Siegel K., and Brückner R. Chem.-Eur. J. 4 (1998) 1116-1121
10. Kim S., Adiyaman Y., Saha G., Powell W.S., and Rokach J. Tetrahedron Lett. 42 (2001) 4445-4448
11. López S., Fermández-Trillo F., Castedo L., and Saá C. Org. Lett. 5 (2003) 3725-3728 and references cited therein
12. Masuda Y., and Mori K. Eur. J. Org. Chem. (2005) 4789-4800
13. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092-4096
14. Riverios R., Rodríguez D., Sestelo J.P., and Sarandeses L.A. Org. Lett. 8 (2006) 1403-1406
15. Ohtaki T., Akasaka K., Kabuto C., and Ohrui H. Biosci. Biotechnol. Biochem. 68 (2004) 153-158
16. Ohrui H. Anal. Sci. 24 (2008) 31-38 and references cited therein
17. 3) δ=85.2, 74.4, 63.2, 41.0, 32.9, 29.5, 29.5, 29.4, 28.6, 25.9, 9.1.
18. Fiandanese V., Bottalico D., Marchese G., and Punzi A. Tetrahedron 60 (2004) 11421-11425