Stereoselective total synthesis of (+)-radicamine B via anti,syn,syn-oxazine

详细信息    查看全文

• 作者：Jin-Seok Kim^&dagger ; ; Gun-Woo Kim^&dagger ; ; Jong-Cheol Kang ; In-Soo Myeong ; Changyoung Jung ; Yong-Taek Lee ; Gyung-Ho Choo ; Seok-Hwi Park ; Gyu-Jin Lee ; Won-Hun Ham ; ^{whham@skku.edu" class="auth_mail" title="E-mail the corresponding author}
• 刊名：Tetrahedron: Asymmetry
• 出版年：2016
• 出版时间：15 March 2016
• 年：2016
• 卷：27
• 期：4-5
• 页码：171-176
• 全文大小：704 K

文摘

The stereoselective total synthesis of (+)-radicamine B was achieved using commercially available d-4-hydroxy-phenylglycine via chiral 1,3-oxazine, which has been applied to synthesis of amino polyols such as DAB-1, d-fagomine, and phytosphingosines. The key steps in this strategy were the palladium(0)-catalyzed stereoselective intramolecular oxazine formation, an extension of the chirality of anti,syn-oxazine with Lewis acid and vinylmagnesium bromide, and pyrrolidine ring formation via hydrogenation reaction. The chiral extension is also applicable to other chiral 1,3-oxazine derived from d-4-hydroxy-phenylglycine.