Synthesis of totarane diterpenes: totarol, maytenoquinone, 6-deoxymaytenoquinone and 8,11,13-totaratriene-12,13-diol.
The syntheses of four totarane diterpenes-totarol, 8,11,13-totaratriene-12,13-diol, 6-deoxymaytenoquinone and maytenoquinone-are described. Totarol was synthesized via cyclization of a modified polyene. 8,11,13-Totaratriene-12,13-diol was prepared from natural totarol by ortho-oxidation with mCBPO (m-chlorobenzoyl peroxide). Maytenoquinone and 6-deoxymaytenoquinone were synthesized from 8,11,13-totaratriene-12,13-diol. 1H-NMR analysis showed that tautomeric isomerization between 6-deoxymaytenoquinone (2-hydroxy-4-quinone methide) and the ortho-quinone was very slow.
Tada
Masahiro
M
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, Japan. tada@cc.tuat.ac.jp
Kurabe
Jun
J
Yasue
Hiroaki
H
Ikuta
Tomohisa
T
D045784:Abietanes; D000478:Alkylation; D000890:Anti-Infective Agents / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry*; D031684:Harpagophytum / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared
C528519:6-deoxymaytenoquinone; C528520:8,11,13-totaratriene-12,13-diol; D045784:Abietanes; D000890:Anti-Infective Agents; D004224:Diterpenes; D007202:Indicators and Reagents; C528518:maytenoquinone; C078548:totarol