Journal of the American Chemical Society

The Synthesis of a Lactone Related to Auxin b1

EB Reid, WR Ruby

Index: Reid; Ruby Journal of the American Chemical Society, 1951 , vol. 73, p. 1054,1058

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Citation Number: 15

Abstract

As a possible direct route to the synthesis of coinpounds related to auxin b, the Reformatsky reaction between ethyl y-bromo-@-ethoxycrotonate and benzaldehyde was investigated. This reaction is shown to form 4-ethoxy-6-phenyl-5, 6-dihydro-% pyrone. The latter, on loss of its ethoxy group, gives 4-hydroxy-6-pheny1-5, 6-dihydro-Z-pyrone, which is the phenyl analog of auxin b, in enol-lactone form. Attempts to prepare the open chain P-keto- ...