D-葡萄糖胺衍生的合成子用于 L-苏式鞘氨醇碱基的组装。根皮素 C 的全合成。
D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.
机构信息
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
出版信息
J Org Chem. 2013 Jan 18;78(2):498-505. doi: 10.1021/jo302355t. Epub 2012 Dec 27.
Abstract
A five-step transformation of D-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of L-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, "two-headed" sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.
摘要
描述了一种将 D-葡萄糖胺五步法转化为（R,R）-2-氨基己-5-烯-1,3-二醇的方法，该方法起始于无需分离中间体的铟介导的 Barbier 反应，产率为 45-51%。后者是组装 L-苏式鞘氨醇碱基的有用前体：长链氨基烷醇和氨基烷二醇，其构型与哺乳动物 D-赤式鞘氨醇相反，但在无脊椎动物衍生的鞘脂中很常见。该方法的实用性通过天然产物 Rhizochalina incrustata 中 Rhizochalinin C 的第一个全合成得到了证明，Rhizochalinin C 是海洋海绵 Rhizochalina incrustata 中天然产物 Rhizochalin C 的长链“双头”鞘氨醇碱基糖苷配基。
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