Synthesis of asymmetrically substituted scyllo-inositol

TETRAHEDRON LETTERS

卷:57

Article

Rodriguez, Jacob¹  Walczak, Maciej A.¹ 

[1] Univ Colorado, Dept Chem & Biochem, Campus Box 215, Boulder, CO 80309 USA

关键词: scyllo-Inositol;    Ferrier rearrangement;    Inositols;   

DOI  :  10.1016/j.tetlet.2016.06.038

来源: Elsevier

【 摘 要 】

scyllo-Inositol, a rare member of the inositol family, is present in axinelloside A, a marine metabolite with interesting inhibitory activity against human telomerase. Here, we present a concise synthesis of asymmetrically substituted scyllo-inositol starting from inexpensive n-glucose. Our synthetic approach capitalizes on Ferrier rearrangement of vinyl acetate and stereoselective reduction of the resultant ketone to establish the scyllo-inositol core. The protocol provides access to large quantities of scyllo-inositol in 10 steps from commercially available materials. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

Free