Synthesis p. 1167 - 1169 (1990)
Update date:2022-07-29
Topics:
Kanemasa
Otsuka
Doi
Tsuge
Wada
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.
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Doi:10.1039/c1jm12071a
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(2011)Doi:10.1002/anie.201103007
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