Synthesis of (R)-curcumene and (R)-xanthorrizol based on 1,2-aryl migration via phenonium ion

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 9, 2007, Pages 1361-1364

  Ehara, Takeru ^a,b   Tanikawa, Shin ^a   Ono, Machiko ^c   Akita, Hiroyuki ^a  

^a TOHO UNIVERSITY   (Japan)

^b NOVARTIS PHARMA K K   (Japan)

^c INTERNATIONAL UNIVERSITY OF HEALTH AND WELFARE   (Japan)

Author keywords

(R) ( ) curcumene; (R) ( ) xanthorrizol; 1,2 aryl migration; Phenonium ion; Solvolysis

Indexed keywords

2 HYDROXY 2 METHYL 6 (3' HYDROXY 4' METHYLPHENYL)HEPTANE; 2 HYDROXY 2 METHYL 6 (4' METHYLPHENYL)HEPTANE; ALCOHOL DERIVATIVE; ANTINEOPLASTIC AGENT; BORONIC ACID DERIVATIVE; CURCUMENE; IODINE DERIVATIVE; METHYL (3' 4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLANYL 4' METHYLPHENYL)HEXANOIC ACID; METHYL (3' HYDROXY 4' METHYLPHENYL)HEXANOIC ACID; METHYL (3' IODO 4' METHYLPHENYL)HEXANOIC ACID; METHYL (4' HYDROXYPHENYL)HEXANOIC ACID; METHYL (4' METHOXYPHENYL)HEXANOIC ACID; METHYL (4' METHYLPHENYL)HEXANOIC ACID; METHYL (4' TRIFLUOROMETHANESULFONYLOXYPHENYL)HEXANOIC ACID; METHYL 4 (4' METHOXYPHENYL) 5 TOSYLOXY HEXENOIC ACID; METHYL 4 CHLORO 5 (4' METHOXYPHENYL) HEXENOIC ACID; METHYL ANTI 4 (4' METHOXYPHENYL) 5 HYDROXY HEXENOIC ACID; METHYL ANTI 4 (4' METHOXYPHENYL) 5 TOSYLOXY HEXENOIC ACID; NATURAL PRODUCT; PHENONIUM; UNCLASSIFIED DRUG; XANTHORRIZOL;

ARTICLE; DEHYDRATION; DRUG STRUCTURE; DRUG SYNTHESIS; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVOLYSIS;

BORONIC ACIDS; CATIONS; CHROMATOGRAPHY, THIN LAYER; CURCUMIN; INDICATORS AND REAGENTS; IODIDES; MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; SOLVENTS;

EID: 34548685324     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.1361     Document Type: Article

References (16)

1. For recent references, see the following cited therein. Hagiwara H., Okabe T., Ono H., Kamat V. P., Hoshi T., Suzuki T., Ando M., J. Chem. Soc., Perkin Trans. I, 2002, 895-900 (2002).
2. Rimpler H., Hansel R., Kochendoerfer L., Z. Naturforsch, 25b, 995 (1970).
3. Itokawa H., Hirayama F., Funakoshi K., Takeya K., Chem. Pharm. Bull., 33, 3488-3491 (1985).
4. Yamazaki M., Maebayashi Y., Iwase N., Kaneko T., Chem. Pharm. Bull., 36, 2070-2074 (1988).
5. For recent references, see the following cited therein. Zhang A., Rajan-Babu T. V., Org. Lett., 6, 3159-3161 (2004).
6. Meyers A. I., Stoianova D., J. Org. Chem., 62, 5219-5221 (1997).
7. Sato K., Bando T., Shindo M., Shishido K., Heterocycles, 50, 11-15 (1999).
8. Ono M., Ehara T., Yokoyama H., Ohtani N., Hoshino Y., Akita H., Chem. Pharm. Bull., 53, 1259-1265 (2005).
9. Akita H., Umezawa I., Takano M., Matsukura H., Oishi T., Chem. Pharm. Bull., 39, 3094-3096 (1991).
10. Akita H., Umezawa I., Takano M., Ohyama C., Matsukura H., Oishi T., Chem. Pharm. Bull., 41, 55-63 (1993).
11. Akita H., Umezawa I., Takano M., Oishi T., Chem. Pharm. Bull., 41, 680-684 (1993).
12. Ono M., Saotome C., Akita H., Tetrahedron: Asymmetry, 7, 2595-2602 (1996).
13. Nishide K., Ohsugi S., Miyamoto T., Kumar K., Node M., Monatsh. Chem., 135, 189-200 (2004).
14. Honda Y., Sakai M., Tsuchihashi G., Chem. Lett., 1985, 1153-1156 (1985).
15. Stavber S., Kralj P., Zupan M., Synthesis, 2002, 1513-1518 (2002).
16. Liu X., Synlett, 2003, 2442-2443 (2003).