182699-79-2Relevant academic research and scientific papers
Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of Keto Acids with Oxo-Tethered Ruthenium Catalysts
Touge, Taichiro,Sakaguchi, Kazuhiko,Tamaki, Nao,Nara, Hideki,Yokozawa, Tohru,Matsumura, Kazuhiko,Kayaki, Yoshihito
, p. 16354 - 16361 (2019/10/16)
A straightforward asymmetric construction of chiral fused γ- and δ-lactones containing multiple contiguous stereocenters was successfully developed by either (1) the dynamic kinetic resolution-asymmetric transfer hydrogenation (DKR-ATH) reaction using oxo
Natural p-menthene monoterpenes: Synthesis of the enantiomeric forms of wine lactone, epi-wine lactone, dill ether, and epi-dill ether starting from a common intermediate
Serra, Stefano,Fuganti, Claudio
, p. 2100 - 2109 (2007/10/03)
A concise synthesis of the enantiomeric forms of wine lactone (5), epi-wine lactone (14), dill ether (6), and epi-dill ether (15) was accomplished starting from the enantiomeric forms of p-mentha-1,8(10)-diene-3,9-diol (8) (Scheme 3). The latter compounds were previously prepared in high optical purity by means of lipase-mediated kinetic resolution, and they were the common building blocks for this divergent synthesis. The key steps were a number of chemo- and diastereoselective reactions of which the oxidation of 8 to the lactone 7 (see Table 1), the diastereoselective reduction of 7 to the lactones 14 and 5 (see Table 2), and the reduction of enolether 16 to ether 15 were studied comprehensively. The effectiveness of this new synthetic approach allows the preparation of the title p-menthane monoterpenes, which are of considerable interest to the perfume industry, in high yield and in a few simple experimental steps.
131. Determination of the configuration of wine lactone
Guth, Helmut
, p. 1559 - 1571 (2007/10/03)
The intense sweet and coconut-like smelling odorant 1, named 'wine lactone', was isolated from different wine varieties. The chemical structure of this compound, which has not yet been detected in wine or a food, was identified by high-resolution mass spe
