通过双环化过程对（±）-盐霉素A、（±）-肉桂酰胺A及其衍生物进行简洁的全合成：对生物合成途径有何启示？
Concise total synthesis of (+/-)-salinosporamide A, (+/-)-cinnabaramide A, and derivatives via a bis-cyclization process: implications for a biosynthetic pathway?
作者信息
Ma Gil, Nguyen Henry, Romo Daniel
机构信息
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
出版信息
Org Lett. 2007 May 24;9(11):2143-6. doi: 10.1021/ol070616u. Epub 2007 May 4.
Abstract
4-Alkylidene-beta-lactones (hetero ketene dimers) and alpha-amino acids are useful precursors for total syntheses of the beta-lactone-containing proteasome inhibitors salinosporamide A, cinnabaramide A, and derivatives. A key step is a nucleophile-promoted, bis-cyclization of keto acids that simultaneously generates the gamma-lactam and beta-lactone of these natural products. This reaction sequence may have implications for the biosynthesis of these natural products.
摘要
4-亚烷基-β-内酯（杂环烯酮二聚体）和α-氨基酸是用于全合成含β-内酯的蛋白酶体抑制剂盐孢霉素A、肉桂酰胺A及其衍生物的有用前体。关键步骤是亲核试剂促进的酮酸双环化反应，该反应同时生成这些天然产物的γ-内酰胺和β-内酯。这一反应序列可能对这些天然产物的生物合成有影响。
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