School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.
Org Lett. 2011 Jun 3;13(11):2900-3. doi: 10.1021/ol200917s. Epub 2011 May 11.
Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the 'amine' component, proceed with high stereoselectivity to produce β,γ-dehydrohomoarylalanine derivatives. Subsequent asymmetric dihydroxylation under neutral conditions gives the corresponding protected β,γ-dihydroxyhomoarylalanines with up to 15:1 dr. The method has been exploited in the efficient, stereoselective synthesis of protected β,γ-dihydroxyhomotyrosine, a component of the antifungal cyclic peptide echinocandin B.
取代苯乙烯基硼酸和乙醛酸的 Petasis 反应，采用叔丁基亚磺酰胺作为“胺”组分，具有高立体选择性，生成β,γ-脱氢同芳基丙氨酸衍生物。随后在中性条件下进行不对称二羟基化反应，以高达 15:1 的 dr 得到相应的保护β,γ-二羟基同芳基丙氨酸。该方法已被用于高效、立体选择性合成保护的β,γ-二羟基同酪氨酸，这是抗真菌环肽 echinocandin B 的一个组成部分。
