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Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

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journal contribution
posted on 18.06.2009, 00:00 by Christoph Schnabel, Martin Hiersemann
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.