Synthesis of totarane diterpenes: Totarol, maytenoquinone, 6-deoxymaytenoquinone and 8,11,13-totaratriene-12,13-diol

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 3, 2008, Pages 287-291

  Tada, Masahiro ^a   Kurabe, Jun ^a   Yasue, Hiroaki ^a   Ikuta, Tomohisa ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Maytenoquinone; Polyene cyclization; Quinone methide; Synthesis; Tautomeric isomerization; Totarol

Indexed keywords

3 CHLOROBENZOYL PEROXIDE; 6 DEOXYMAYTENOQUINONE; 8,11,13 TOTARATRIENE 12,13 DIOL; DITERPENE; MAYTENOQUINONE; PEROXIDE; POLYENE; TOTAROL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ALKYLATION; ANTI-INFECTIVE AGENTS; CHROMATOGRAPHY, THIN LAYER; CYCLIZATION; DITERPENES; HARPAGOPHYTUM; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, INFRARED;

EID: 41549134341     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.287     Document Type: Article

References (28)

1. Yang Z., Kitano Y., Chiba K., Shibata N., Kurokawa H., Doi Y., Arakawa Y., Tada M., Bioorg. Med. Chem., 9, 347-356 (2001).
2. Dellar J. E., Cole M. D., Waterman P. G., Phytochemistry, 41, 735-738 (1996).
3. Tada M., Ishimaru K., Chem. Pharm. Bull., 54, 1412-1417 (2007).
4. Kupchan S. M., Karim A., Marcks C., J. Am. Chem. Soc., 90, 5923-5924 (1968).
5. Kupchan S. M., Karim A., Marcks C., J. Org. Chem., 34, 3912-3918 (1969).
6. Lin L., Blasko G., Cordell G. A., Phytochemistry, 28, 177-181 (1989).
7. Sabri N. N., Abou-donia A. A., Assad A. M., Ghazy N. M., El-lakang A. M., Tempesta M. S., Sanson D. R., Planta Med., 55, 582-582 (1989).
8. Himejima M., Kubo I., J. Agric. Food Chem., 39, 418-421 (1991).
9. Muroi H., Kubo I., Biosci. Biotechnol. Biochem., 58, 1925-1926 (1994).
10. Haraguti H., Oike S., Muroi H., Kubo I., Planta Med., 62, 122-125 (1996).
11. Tezuka Y., Kasimu R., Li J. X., Basnet P., Tanaka K., Namba T., Kadota S., Chem. Pharm. Bull., 46, 107-112 (1998).
12. Harrison L. J., Asakawa Y., Phytochemistry, 26, 1211-1212 (1987).
13. Sharp H., Latif Z., Bartholomew B., Bright C., Jones C., Sarker S., Biochem. Syst. Ecol., 29, 215-217 (2001).
14. He K., Zeng L., Shi G., Ghao G., Kolzowski J., Mclaughlin J., J. Nat. Prod., 60, 38-40 (1997).
15. Ulubelen A., Öksüz S., Kolak U., Birman H., Voelter W., Planta Med., 66, 627-629 (2000).
16. González A., Aguiar Z., Grillo T., Luis J., Phytochemistry, 31, 1691-1695 (1992).
17. Clarkson C., Campbell W. E., Smith P., Planta Med., 69, 720-724 (2003).
18. Ulubelen A., Evren N., Tuziaci E., Bozok-Johansson C., J. Nat. Prod., 51, 1178-1183 (1988).
19. Evans G. B., Furneaux R. H., Gravestock M. B., Lynch G. P., Scott G. K., Bioorg. Med. Chem., 7, 1953-1964 (1999).
20. Barltrop J. A., Roger N. A. J., J. Chem. Soc., 1958, 2566-2572 (1958).
21. Matsumoto T., Suetsugu A., Bull. Chem. Soc. Jpn., 52, 1450-1453 (1979).
22. Marcos I. S., Cubillo M. A., Moro R. F., Diez D., Basabe P., Sanz F., Urones J. G., Tetrahedron Lett., 44, 8831-8835 (2003).
23. Clarkson C., Campbell W. E., Smith P., Planta Med., 69, 720-724 (2003).
24. Martin J. D., Tetrahedron, 29, 2553-2559 (1973).
25. Matsumoto T., Ohmura T., Usui S., Bull. Chem. Soc. Jpn., 52, 1957-1963 (1979).
26. Harrison L., Asakawa Y., Phytochemistry, 26, 1211-1212 (1987).
27. Burnell R. H., Jean M., Marceau S., Can. J. Chem., 66, 227-230 (1988).
28. Tada M., Nishiiri S., Yang Z., Imai Y., Tajima S., Okazaki N., Kitano Y., Chiba K., J. Chem. Soc. Perkin Trans. 1, 2000, 2657-2664 (2000).