- An efficient and simple synthesis of (-)-wine lactone
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A short and efficient diastereoselective snythesis of(-)-wine lactone (-)-4a involving FeCl3/NaI-mediated iodolactonization of γδ-unsaturated acid 7 as the key step is described.
- Chavan, Subhash P.,Kharul, Rajendra K.,Sharma, Anil K.,Chavan, Sambhaji P.
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- Concise enantioselective synthesis of wine lactone via intramolecular Diels-Alder reaction
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An enantioselective synthesis of (3S,3aS,7aR)-wine lactone, a major aroma component of white wine and citrus juices, was achieved starting from (S)-2-methyl-3-butenoic acid. An intramolecular Diels-Alder reaction was employed as a key step.
- Masuda, Yui,Ogura, Yusuke,Ohkubo, Yasutaka,Takikawa, Hirosato,Watanabe, Hidenori
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p. 1390 - 1394
(2021/08/13)
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- 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
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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
- Touge, Taichiro,Sakaguchi, Kazuhiko,Tamaki, Nao,Nara, Hideki,Yokozawa, Tohru,Matsumura, Kazuhiko,Kayaki, Yoshihito
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p. 16354 - 16361
(2019/10/16)
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- PROCESS FOR PRODUCING WINE LACTONE
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The present invention relates to a method comprising (A) reacting a β-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl
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Paragraph 0443-0454
(2013/03/26)
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- PROCESSES FOR PRODUCTION OF WINE LACTONE AND ITS INTERMEDIATES AND APPLICATION OF THE LACTONE
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The present invention provides a method for producing wine lactone, a method for producing intermediates that are usable in production of wine lactone, and techniques for the application of wine lactone. The method for producing the wine lactone (Compound
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Page/Page column 11
(2008/06/13)
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- 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
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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.
- Serra, Stefano,Fuganti, Claudio
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p. 2100 - 2109
(2007/10/03)
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- Synthesis of enantiomerically pure (-)-wine lactone based on a palladium-catalyzed enantioselective allylic substitution
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The first enantioselective synthesis of enantiomerically pure (-)-wine lactone, (-)-1a, a fragrance constituent of various white wines, and its epimer (+)-1b, was carried out. The key steps are allylic substitution of (±)-2-cyclohexen-1-yl acetate (2) wit
- Bergner,Helmchen, Guenter
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p. 419 - 423
(2007/10/03)
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- 131. Determination of the configuration of wine lactone
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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
- Guth, Helmut
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p. 1559 - 1571
(2007/10/03)
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