通过缩水甘油醛衍生支架的环收缩探索骨骼多样性。
Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.
作者信息
Yeager Adam R, Min Geanna K, Porco John A, Schaus Scott E
机构信息
Department of Chemistry, Center for Chemical Methodology and Library Development at Boston University, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, MA 02215, USA.
出版信息
Org Lett. 2006 Oct 26;8(22):5065-8. doi: 10.1021/ol0618252.
Aryl ether C-glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0). The aryl ethers were subjected to either [3,3]-sigmatropic rearrangement to produce 3-pyranyl-phenols or Au(III)-mediated ring contraction to create highly substituted tetrahydrofurans. [structure: see text]
芳基醚C-糖苷支架已由三-O-乙酰基-D-葡糖醛通过C-糖基化制备，随后通过Pd(0)介导的酚类进行烯丙基取代。芳基醚经过[3,3]-σ迁移重排以生成3-吡喃基酚，或经过Au(III)介导的环收缩以生成高度取代的四氢呋喃。[结构：见原文]
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