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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-other | 2010 Aug

REPOSITORIES: biostudies-other

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

Jeso Valer V   Micalizio Glenn C GC  

Journal of the American Chemical Society 20100801 33

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. ...[more]

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