Total synthesis of jatrophane diterpenes from Euphorbia characias.
The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.
Schnabel
Christoph
C
Fakultät Chemie, Technische Universität Dortmund, 44227 Dortmund, Germany.
Hiersemann
Martin
M
D003432:Cross-Linking Reagents; D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D028481:Euphorbia / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003432:Cross-Linking Reagents; D003517:Cyclopentanes; D004224:Diterpenes; D010936:Plant Extracts; C530345:jatrophane