Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Joshua R. Sacher; Steven M. Weinreb

doi:10.1016/j.tet.2011.04.016

Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Joshua R. Sacher, Steven M. Weinreb

Chemistry

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7 Scopus citations

Abstract

A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective DielseAlder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration.

Original language	English (US)
Pages (from-to)	10203-10207
Number of pages	5
Journal	Tetrahedron
Volume	67
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2011.04.016
State	Published - Dec 30 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.04.016

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title = "Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H",

abstract = "A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective DielseAlder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration.",

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note = "Funding Information: We gratefully acknowledge financial support from the National Science Foundation ( CHE-0806807 ). We also wish to thank Dr. H. Yennawar (Penn State Small Molecule X-ray Crystallographic Facility) for the X-ray structure determinations. 13 ",

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AU - Sacher, Joshua R.

AU - Weinreb, Steven M.

N1 - Funding Information: We gratefully acknowledge financial support from the National Science Foundation ( CHE-0806807 ). We also wish to thank Dr. H. Yennawar (Penn State Small Molecule X-ray Crystallographic Facility) for the X-ray structure determinations. 13

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Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

Abstract

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