A novel method for the synthesis of spiroketal systems. Synthesis of the pheromones of the common wasp and the olive fruit fly

Total syntheses of the pheromones of the common wasp and the olive fruit fly were accomplished by a strategy in which the key transformation involved the cleavage of tetrahydrofuran with (tert-butyldimethyl-sily)manganese pentacarbonyl followed by sequential insertion of ethyl acrylate.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 56; no. 10; pp. 3207 - 3210
Main Authors DeShong, Philip, Rybczynski, Philip J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.05.1991
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
CHEMISTRY
CARBONYL-COMPOUNDS
ORGANOMANGANESE PENTACARBONYL COMPLEXES
BUTENOLIDES
CHEMICAL-SHIFTS
STEREOSELECTIVE SYNTHESIS
Stereoselectivity
Acetal
Insertion
Lactone
Photochemical reaction
Oxygen heterocycle
Scission
Spiran
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Summary:Total syntheses of the pheromones of the common wasp and the olive fruit fly were accomplished by a strategy in which the key transformation involved the cleavage of tetrahydrofuran with (tert-butyldimethyl-sily)manganese pentacarbonyl followed by sequential insertion of ethyl acrylate.
Bibliography:istex:F6284FE77C5565967AFD95C745AFDF44E179B036
ark:/67375/TPS-M5KG70S5-X
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00010a005