A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction of a densely functionalized diene

The key step in a formal total synthesis of eleutherobin was an unprecedented kinetically controlled RCM reaction of a densely functionalized diene 1 bearing two PMP-protected allylic alcohols in the presence of a second-generation Grubbs catalyst. Subsequent isomerization of the E 10-membered enedione 2 to the more stable 2 isomer and cleavage of the MOM protecting group led to the known precursor 3. MOM = methoxymethyl; PMP = p-methoxyphenyl.