Synthetic studies toward jatrophane diterpenes from Euphorbia characias. Enantioselective synthesis of (-)-15-O-acetyl-3-O-propionyl-17-norcharaciol.
The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.
Helmboldt
Hannes
H
Fakultät Chemie, Technische Universität Dortmund, Dortmund 44227, Germany.
Hiersemann
Martin
M
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003517:Cyclopentanes / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D004952:Esters / Q000737:chemistry; D028481:Euphorbia / Q000737:chemistry*; D006801:Humans; D013237:Stereoisomerism; D013379:Substrate Specificity
C516000:15-acetyl-3-propionyl-17-norcharaciol; D003517:Cyclopentanes; D004224:Diterpenes; D004952:Esters; C530345:jatrophane