Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 33, Pages 11422-11424Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja104782u
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Funding
- American Cancer Society [RSG-06-117-01]
- National Institutes of Health-NIGMS [GM80266]
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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-allyne complex and a pyrone-containing allylic alcohol.
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