Liebigs Annalen der Chemie

… Compounds, XXXVIII. Ring Enlargement of Cyclodecanone by a Chiral Building Block: Synthesis and Olfactory Properties of (12R)??(+)??12??Methyl??13??Tridecanolide

P Kraft, W Tochtermann

Index: Kraft, Philip; Tochtermann, Werner Liebigs Annalen der Chemie, 1994 , # 12 p. 1161 - 1164

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Citation Number: 8

Abstract

Abstract The title compound (+)-3 was synthesized in four steps by ring enlargement of cyclodecanone (6) with the chiral building block 5. The protected hydroxy halide 5, easily prepared from commercially available (2S)-(+)-methyl 3-hydroxy-2-methylpropanoate (4), was introduced by HMPA-mediated enolate alkylation and subsequent formation of the cyclic enol ether 8. Ozonolysis and mild chemoselective reduction of the carbonyl function ...