Total synthesis of jatrophane diterpenes from Euphorbia characias.

Christoph Schnabel, Martin Hiersemann

Fakultät Chemie, Technische Universität Dortmund, 44227 Dortmund, Germany.

Organic letters 2009 Jun 18

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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.

Citation

Christoph Schnabel, Martin Hiersemann. Total synthesis of jatrophane diterpenes from Euphorbia characias. Organic letters. 2009 Jun 18;11(12):2555-8