Total synthesis of lehualide B by allylic alcohol-alkyne reductive cross-coupling.

ABSTRACT: The total synthesis of anticancer marine natural product lehualide B is described. Overall, the synthesis proceeds in just eight steps from a simple gamma-pyrone, does not require the use of protecting groups, and delivers each nonconjugated trisubstituted alkene with high levels of stereoselection. The challenging C12-C16 bis-trisubstituted 1,4-diene was installed with a complex reductive cross-coupling reaction between a preformed Ti-alkyne complex and a pyrone-containing allylic alcohol.

SUBMITTER: Jeso V 

PROVIDER: S-EPMC2923668 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature