2- and 8- functionalized 1,4,7,10-tetraoxaspiro[5.5]undecanes. I. Synthesis of (±)-E,E and (±)-Z,E structures

The synthesis of (±)-E,E and (±)-Z,E 2,8-dihydroxymethyl-1,4,7,10-tetraoxaspiro[5.5]undecane is described. The selective modification of one sidechain is examined for the (±)-E,E isomer, and a tetraoxygenated analogue of a commonly encountered insect pheromone is prepared. Synthesis of title compoun...

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Bibliographic Details
Published inTetrahedron Vol. 49; no. 13; pp. 2621 - 2628
Main Authors Lemaire, Marielle, Jeminet, Georges, Gourcy, Jean-Gabriel, Dauphin, Gérard
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 26.03.1993
Elsevier
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Stereoselectivity
Racemate
Acetal
Oxygen heterocycle
Six membered ring
Spiran
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Summary:The synthesis of (±)-E,E and (±)-Z,E 2,8-dihydroxymethyl-1,4,7,10-tetraoxaspiro[5.5]undecane is described. The selective modification of one sidechain is examined for the (±)-E,E isomer, and a tetraoxygenated analogue of a commonly encountered insect pheromone is prepared. Synthesis of title compounds has been achieved starting from (±)-diisopropylidene triglycerol
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)86341-9