A convergent approach toward phoslactomycins and leustroducsins

详细信息    查看全文

• 作者：Valé ; rie Druais ; Michael J. Hall ; Camilla Corsi ; Sebastian V. Wendeborn ; Christophe Meyer ; Janine Cossy
• 关键词：Phoslactomycins ; Leustroducsins ; Metathesis reactions ; Noyori reduction ; Wittig rearrangement
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：14 August 2010
• 年：2010
• 卷：66
• 期：33
• 页码：6358-6375
• 全文大小：931 K

文摘

Synthetic studies devoted to the development of a convergent approach toward phoslactomycins and leustroducsins, a family of natural products inhibitors of serine/threonine phosphatase 2A, are reported. A formal synthesis of phoslactomycin B was achieved in which the key steps are a [2,3]-Wittig rearrangement to control the C4 and C5 stereocenters, a diastereoselective addition of an acetylenic Grignard reagent to an α-alkoxy ketone to create the C8 tertiary alcohol, and a relay ring-closing metathesis to construct the α,β-unsaturated δ-lactone. In this approach, all the stereocenters originate, either directly or indirectly, from catalytic enantioselective reductions of acetylenic ketones.