Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D
Ding-Yah Yang, Kiran B. Manjappa, Jhih-Min Lin
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01061

DOI: 10.1021/acs.joc.7b01061

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