Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange
oleh: Samuel W. J. Shields, Peter H. Buist, Jeffrey M. Manthorpe
| Format: | Article |
|---|---|
| Diterbitkan: | Georg Thieme Verlag KG 2018-04-01 |
Deskripsi
Abstract The total synthesis of isotopically labelled (9R,10S)-dihydrosterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenching of a lithium-sulfoxide exchange was required to achieve the requisite high levels of deuterium incorporation.