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 Z isomer and cleavage of the MOM protecting group led to the known precursor 3. MOM=methoxymethyl; PMP=p-methoxyphenyl.
A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction of a densely functionalized diene / D. Castoldi, L. Caggiano, L. Panigada, O. Sharon, A.M. Costa, C. Gennari. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - 44:4(2005), pp. 588-591.
A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction of a densely functionalized diene
L. Panigada;C. GennariUltimo
2005
Abstract
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 Z isomer and cleavage of the MOM protecting group led to the known precursor 3. MOM=methoxymethyl; PMP=p-methoxyphenyl.Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.