1160556-85-3Relevant academic research and scientific papers
Total synthesis of natural and non-natural δ 5,6δ12,13-jatrophane diterpenes and their evaluation as MDR modulators
Schnabel, Christoph,Sterz, Katja,Mueller, Henrik,Rehbein, Julia,Wiese, Michael,Hiersemann, Martin
body text, p. 512 - 522 (2011/04/22)
We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.
Total synthesis of jatrophane diterpenes from euphorbia characias
Schnabel, Christoph,Hiersemann, Martin
supporting information; experimental part, p. 2555 - 2558 (2009/10/02)
The enantioselective total synthesis of the jatrophane diterpene (-)-15-0-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 ass
