Stereoselective total synthesis of chrysanthemol.
Chrysanthemol (1), a trans-eudesmane type sesquiterpene from Chrysanthemum indicum L., possesses certain anti-inflammatory activity. Its total synthesis was approached from two alternative routes and finally accomplished in ten steps from R-(+)-carvone via alpha-eudesmol (10) as the key intermediate. The overall yield is 2.4% and the spectral data of the synthetic target compound were identical with that of natural chrysanthemol (1). Seven intermediary compounds were tested for inhibitory effects on the carragenan-induced swelling of mouse paw but demonstrated no obvious activities.
Mou
L Y
LY
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing.
Zhu
L Y
LY
Lin
Z Y
ZY
Liang
X T
XT
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000627:therapeutic use; D002681:China; D011723:Chrysanthemum cinerariifolium / Q000737:chemistry*; D000081005:Cyclohexane Monoterpenes; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D039821:Monoterpenes; D008517:Phytotherapy; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D045787:Sesquiterpenes, Eudesmane; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000081005:Cyclohexane Monoterpenes; D004365:Drugs, Chinese Herbal; D039821:Monoterpenes; D045787:Sesquiterpenes, Eudesmane; D013729:Terpenes; C118684:alpha-eudesmol; C056121:chrysanthemol; C006923:carvone