Stereoselective total syntheses of uncommon sesquiterpenoids isolated from Jatropha neopauciflora.
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]nonenone framework possessing an angular methyl group but also a highly stereoselective construction of the isopropylcyclopropane ring.
Hayashi
Yujiro
Y
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, Japan.
Miyakoshi
Naoki
N
Kitagaki
Shinji
S
Mukai
Chisato
C
D002384:Catalysis; D003500:Cyclization; D031286:Jatropha / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification
D012717:Sesquiterpenes; D012238:Rhodium