Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Org Lett. 2011 Sep 2;13(17):4652-5. doi: 10.1021/ol201863b. Epub 2011 Aug 11.
A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C(2)-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.
本文描述了(+)-SCH 351448(1)的一种会聚合成方法,(+)-SCH 351448(1)为 C(2)对称的大环二醇单钠盐。我们的方法基于[4 + 2]环加成反应,使用手性烯丙基硅烷(anti-5c)来组装吡喃亚基。同型二聚体以分步的方式进行;在 C29'处进行初始酯化,然后在 C29 处进行大环化,得到所需的大环二醇。