Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D.

An efficient construction of phenyl-substituted coumarin-pyrrole-isoquinoline-fused pentacycle via base-promoted Grob-type coupling of 3-nitrocoumarin and papaverine in a sealed tube is reported. This reaction is further applied to the total synthesis of lamellarin H in three linear steps and lamellarin D in eight linear steps with overall yields of 31% and 14%, respectively.

Citation

Kiran B Manjappa, Jhih-Min Lin, Ding-Yah Yang. Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D. The Journal of organic chemistry. 2017 Jul 21;82(14):7648-7656

PMID: 28665125

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