gymnodimine and tetrahydrofuran

gymnodimine has been researched along with tetrahydrofuran* in 2 studies

Other Studies

2 other study(ies) available for gymnodimine and tetrahydrofuran

Article	Year
Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization. Organic & biomolecular chemistry, 2011, May-21, Volume: 9, Issue:10 A straightforward access to the C10-C20 skeleton of gymnodimine, incorporating a tetrahydrofuran fragment, is described. The elaboration of the THF moiety is based on a stereocontrolled Ueno-Stork cyclization. A Lewis-acid mediated allylation of the resulting acetal at C13 and a Horner-Wadsworth-Emmons olefination on the ketone at C17 complete the synthesis. Topics: Catalysis; Cyclization; Furans; Heterocyclic Compounds, 3-Ring; Hydrocarbons, Cyclic; Imines; Stereoisomerism	2011
Studies on the synthesis of gymnodimine. Stereocontrolled construction of the tetrahydrofuran subunit. Organic letters, 2003, Oct-30, Volume: 5, Issue:22 [reaction: see text]. A bis-(2,6-dichlorobenzyl) ether is shown to undergo efficient and highly stereoselective intramolecular iodoetherification to yield a cis-2,5-disubstituted tetrahydrofuran, thus providing a powerful illustration of a stereodirecting effect first noted by Rychnovsky and Bartlett. The tetrahydrofuran was transformed into a subunit suitable for incorporation into the shellfish toxin gymnodimine. Topics: Crystallography, X-Ray; Cyclization; Furans; Heterocyclic Compounds, 3-Ring; Hydrocarbons, Cyclic; Imines; Iodine; Molecular Conformation; Molecular Structure; Stereoisomerism	2003

Article

Year

Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization.

Organic & biomolecular chemistry, 2011, May-21, Volume: 9, Issue:10

A straightforward access to the C10-C20 skeleton of gymnodimine, incorporating a tetrahydrofuran fragment, is described. The elaboration of the THF moiety is based on a stereocontrolled Ueno-Stork cyclization. A Lewis-acid mediated allylation of the resulting acetal at C13 and a Horner-Wadsworth-Emmons olefination on the ketone at C17 complete the synthesis.

Topics: Catalysis; Cyclization; Furans; Heterocyclic Compounds, 3-Ring; Hydrocarbons, Cyclic; Imines; Stereoisomerism

2011

Studies on the synthesis of gymnodimine. Stereocontrolled construction of the tetrahydrofuran subunit.

Organic letters, 2003, Oct-30, Volume: 5, Issue:22

[reaction: see text]. A bis-(2,6-dichlorobenzyl) ether is shown to undergo efficient and highly stereoselective intramolecular iodoetherification to yield a cis-2,5-disubstituted tetrahydrofuran, thus providing a powerful illustration of a stereodirecting effect first noted by Rychnovsky and Bartlett. The tetrahydrofuran was transformed into a subunit suitable for incorporation into the shellfish toxin gymnodimine.

Topics: Crystallography, X-Ray; Cyclization; Furans; Heterocyclic Compounds, 3-Ring; Hydrocarbons, Cyclic; Imines; Iodine; Molecular Conformation; Molecular Structure; Stereoisomerism

2003