Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids

Tetrahedron

Volumn 62, Issue 40, 2006, Pages 9483-9496

  Shirahata, Tatsuya ^a   Sunazuka, Toshiaki ^a,b   Yoshida, Kiminari ^a   Yamamoto, Daisuke ^a   Harigaya, Yoshihiro ^a   Kuwajima, Isao ^b   Nagai, Takayuki ^a,b   Kiyohara, Hiroaki ^a,b   Yamada, Haruki ^a,b   Omura, Satoshi ^a,b  

^a KITASATO UNIVERSITY   (Japan)

^b KITASATO INSTITUTE   (Japan)

Author keywords

Adjuvant; Determination of stereochemistry; Total synthesis

Indexed keywords

HYDROXY FATTY ACID; KAMPO; PINELLIC ACID; SHO SEIRYU TO; UNCLASSIFIED DRUG;

ARTICLE; DIHYDROXYLATION; DRUG SYNTHESIS; FATTY ACID SYNTHESIS; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM;

PINELLIA TERNATA;

EID: 33747789518     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.088     Document Type: Article

References (23)

1. Murphy B.R., and Webster R.G. Orthomyxoviruses. In: Fields B.N., and Knipe D.M. (Eds). Virology. 2nd ed. (1990), Raven, New York, NY 1091-1152
2. Nagai T., and Yamada H. Immunopharmacol. Immunotoxicol. 20 (1998) 267-281
3. Nagai T., and Yamada H. Int. J. Immunopharmacol. 16 (1994) 605-613
4. Nagai T., Urata M., and Yamada H. Immunopharmacol. Immunotoxicol. 18 (1996) 193-208
5. Nagai T., Kiyohara H., Munakata K., Shirahata T., Sunazuka T., Harigaya Y., and Yamada H. Int. Immunopharmacol. 2 (2002) 1183-1193
6. Kato T., Yamaguchi Y., Ohnuma S., Uehara T., Namai T., Kodama M., and Shiobara Y. Chem. Lett. (1986) 577-580
7. Colin D.F., and William S.P. Biochim. Biophys. Acta 754 (1983) 57-71
8. Hanberg M. Lipids 26 (1991) 407-415
9. Harada N., Iwabuchi J., Yokota Y., Uda H., and Nakanishi K. J. Am. Chem. Soc. 103 (1981) 5590-5591
10. Kouda K., Ooi T., Kaya K., and Kusumi T. Tetrahedron Lett. 37 (1996) 6347-6350
11. Uehara H., Oishi T., Yoshikawa K., Mochida K., and Hirama M. Tetrahedron Lett. 40 (1999) 8641-8645
12. For review, see:. Kolb H.C., Van Nieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
13. Grobel B.T., and Seebach D. Synthesis (1977) 357-402
14. Okuma K., Hashimoto S., Ono M., Shioji K., Matsuyama H., and Bestmann H.J. Tetrahedron 54 (1998) 4243-4250
15. 2(PHAL) afforded 12R,13R and the stereoselective reduction with (S)-BINAL-H gave 9S, while the same reduction with (R)-BINAL-H gave 9R, as shown in the following figure: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519. {A figure is presented}{A figure is presented}
16. For review, see:. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986-2012
17. Noyori R., Tomino I., Tanimoto Y., and Nishizawa M. J. Am. Chem. Soc. 106 (1984) 6709-6716
18. Sunazuka T., Shirahata T., Yoshida K., Yamamoto D., Harigaya Y., Nagai T., Kiyohara H., Yamada H., and Ōmura S. Tetrahedron Lett. 43 (2002) 1265-1268
19. For review, see:. Mitsunobu O. Synthesis (1981) 1-28
20. For review, see:. Tsunoda T., and Ito S. J. Synth. Org. Chem. Jpn. 55 (1997) 631-641
21. Corey E.J., Nicolaou K.C., Shibasaki M., Machida Y., and Shiner C.S. Tetrahedron Lett. 37 (1975) 3183-3186
22. Shimizu T., Hiranuma S., and Nakata T. Tetrahedron Lett. 37 (1996) 6145-6148
23. Shirahata T., Sunazuka T., Yoshida K., Yamamoto D., Harigaya Y., Nagai T., Kiyohara H., Yamada H., and Ōmura S. Bioorg. Med. Chem. Lett. 13 (2003) 937-941