Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 21, Pages 8143-8153Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901589e
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- Japan Society for the Promotion of Science (JSPS)
- Japan Science and Technology Agency (JST)
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A general synthetic route to rationally designed lamellarin D analogues, 1-dearyllamellarin D (1)and 1-substituted 1-dearyllamellarin D (2), has been developed. The key pentacyclic Intermediate 22 was prepared by palladium-catalyzed direct arylation of 12, which in turn was synthesized via C-2-selective lithiation of 15 followed by palladium-catalyzed cross-coupling as the key reactions. Compound 22 was converted to a wide range of C-1-substituted analogues 2 via regioselective electrophilic substitution and palladium-catalyzed cross-coupling reactions.
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