Tetrahedron

Macrocyclic musk compounds—IV: New syntheses of α, ω-dicarboxylic and ω-hydroxy acids from undec-10-enoic acid

MSR Nair, HH Mathur, SC Bhattacharyya

Index: Nair,M.S.R. et al. Tetrahedron, 1963 , vol. 19, p. 905 - 909

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Citation Number: 4

Abstract

Undec-10-enoyl chloride on condensation with enamines followed by ring cleavage yielded keto-enoic acids. The latter on Huang-Minlon reduction gave the enoic acids which on oxidation furnished the dioic acids. Ozonization of the enoic acids followed by sodium borohydride reduction of the ozonide yielded ω-hydroxy acids. The C16 and C15 dioic and ω-hydroxy acids, suitable for conversion to macrocyclic ketones and lactones, were thus ...

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