Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions

The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)2-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brownʹs enantioselective allylboration, and Grubbsʹ cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range.