Total synthesis of pyranicin.
Total synthesis of pyranicin.
复制标题
吡喃星的全合成。
作者：
D. Strand;T. Rein
[反应：见正文]提出了番荔枝内酯吡喃菌素（1）的立体控制收敛合成。使用不对称Horner-Wadsworth-Emmons（HWE）反应来获得关键中间体。四氢吡喃衍生物2通过内消旋二醛6的不对称去对称化获得，并且使用涉及平行动力学HWE解析的立体会聚反应序列，然后通过Pd催化的烯丙基取代来构建丁烯二醇片段。使用Carreira的不对称乙炔加成方法安装C10/C15 1，6-二醇基序。
[Reaction: see text] A stereocontrolled convergent synthesis of the annonaceous acetogenin pyranicin (1) is presented. Asymmetric Horner-Wadsworth-Emmons (HWE) reactions were used to access key intermediates. The tetrahydropyran derivative 2 was obtained via an asymmetric desymmetrization of the meso-dialdehyde 6, and the butenolide fragment was constructed using a stereoconvergent reaction sequence involving a parallel kinetic HWE resolution followed by a Pd-catalyzed allylic substitution. The C10/C15 1,6-diol motif was installed using Carreira's asymmetric acetylide addition methodology.
细胞毒性苏式、反式、苏式、反式、苏式乙酰基阿西明及其 C-10 差向异构体的全合成：绝对立体化学的明确证实。
DOI：
10.1021/np990132
发表时间：
1999
期刊：
Journal of natural products.
影响因子：
--
作者：
Marshall,JA;Jiang,H
通讯作者：
Jiang,H