Download PDF
Synthesis 1990; 1990(12): 1167-1169
DOI: 10.1055/s-1990-27125
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of (E)-4-Oxo-5-hexenals and Their Acetal Derivatives

Shuji Kanemasa* , Tatsuya Otsuka, Kenji Doi, Otohiko Tsuge, Eiji Wada
  • *Institute of Advanced Material Study, Kyushu University, Kasugakoen, Kasuga 816, Japan
Further Information

Publication History

Publication Date:
02 May 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

An effective synthesis of (E)-4-oxo-5-hexenals 6 and the acetals 5 starting from ethyl 2-alkoxy-1-cyclopropanecarboxylates 1a-d is presented. The acid-induced ring opening of the cyclopropanecarboxylates 1a, b, followed by phosphorylmethylation or the phosphorylmethylation of the ester 1c followed by ring opening leads to the 5-acetal of 2,5-dioxopentylphosphonate 4. The Horner-Emmons olefination of 4 with various aldehydes produces the title compounds.