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

Kiran B Manjappa; Jhih-Min Lin; Ding-Yah Yang

doi:10.1021/acs.joc.7b01061

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

J Org Chem. 2017 Jul 21;82(14):7648-7656. doi: 10.1021/acs.joc.7b01061. Epub 2017 Jun 30.

Authors

Kiran B Manjappa¹, Jhih-Min Lin¹, Ding-Yah Yang¹

Affiliation

¹ Department of Chemistry, Tunghai University , No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung City 40704, Taiwan, Republic of China.

PMID: 28665125
DOI: 10.1021/acs.joc.7b01061

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Coumarins / chemical synthesis*
Coumarins / chemistry*
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry*
Molecular Structure
Pyrroles / chemistry*
Stereoisomerism

Substances

Coumarins
Heterocyclic Compounds, 4 or More Rings
Isoquinolines
Pyrroles
lamellarin D
lamellarin H
coumarin
isoquinoline