Cycloalkenone synthesis via Lewis acid-catalyzed retro Diels-Alder reactions of norbornene derivatives: synthesis of 12-oxophytodienoic acid (12-oxoPDA)

Norbornene derivatives of type 1 undergo retro Diels-Alder reactions at or below ambient temperature in the presence of methylaluminum dichloride and a reactive dienophile. Application of the [4 + 2] cycloreversion methodology to the synthesis of 12-oxophytodienoic acid 3 is described.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 54; no. 26; pp. 6008 - 6010
Main Authors Grieco, Paul A, Abood, Norman
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.12.1989
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Norbornene derivatives of type 1 undergo retro Diels-Alder reactions at or below ambient temperature in the presence of methylaluminum dichloride and a reactive dienophile. Application of the [4 + 2] cycloreversion methodology to the synthesis of 12-oxophytodienoic acid 3 is described.
Bibliography:istex:F6F4C3583D79B553DD1FC2B50310ACFAD1607CFB
ark:/67375/TPS-F3M2G7J3-M
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00287a005