442913-72-6Relevant articles and documents
First total synthesis of pinolide
Yadav, Jhillu Singh,Avuluri, Srilatha,Kattela, Shiva Shankar,Das, Saibal
, p. 6967 - 6972 (2013)
The first total synthesis of pinolide, a nonsymmetrical ten-membered macrocyclic, is described starting from readily available (-)-tartaric and L-ascorbic acid. The key synthetic steps include Barbier allylation, Yamaguchi esterification and ring-closing metathesis (RCM) reactions. The synthetic strategy has been successful for the construction of the ten-membered core skeleton. A facile and convergent approach enabled the incorporation of all the four stereogenic centers present in the molecule. The first total synthesis of pinolide, a nonsymmetrical ten-membered macrocycle having four stereogenic centers has been demonstrated. The stereoselective approach involves key reaction steps including Barbier allylation, Yamaguchi esterification, and Grubbs' ring-closing metathesis reactions. Copyright
Total synthesis and evaluation of the actin-binding properties of microcarpalide and a focused library of analogues
Fuerstner, Alois,Nagano, Takashi,Mueller, Christoph,Seidel, Guenter,Mueller, Oliver
, p. 1452 - 1462 (2008/02/04)
A comparative investigation shows that hydroxylated 10-membered lactones modeled around the fungal metabolites microcarpalide (1) and pinolidoxin (2) are endowed with selective actin-binding properties. Although less potent than the marine natural product