4.8 Article

Stereoselective total syntheses of uncommon sesquiterpenoids isolated from Jatropha neopauciflora

Journal

ORGANIC LETTERS
Volume 10, Issue 12, Pages 2385-2388

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol800633a

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The first total syntheses of two tricyclic sesquiterpenes 1 and 2, isolated from Jatropha neopauciflora, were completed from dimethyl D-tartrate in a stereoselective manner. The crucial steps in these syntheses involved not only the Rh(I)-catalyzed Pauson-Khand-type reaction of the allenene derivative leading to the exclusive formation of the bicyclo[4.3.0] nonen one framework possessing an angular methyl group but also a highly stereoselective construction of the isopropylcyclopropane ring.

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