Synthesis of the Common Monomeric Unit of Uroleuconaphins and Viridaphins via Hauser-Kraus Annulation

Synthesis of the Common Monomeric Unit of Uroleuconaphins and Viridaphins via Hauser-Kraus Annulation
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通过 Hauser-Kraus 环化合成尿亮白脑苷酸和病毒苷酸的共同单体单元

DOI:
10.1055/a-1334-6982
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发表时间:
2021
期刊:
Synthesis
影响因子:
--
通讯作者:
Hiroto Kaku
Hiroto Kaku
中科院分区:
--
文献类型:
--
作者:
Kei Kitamura;Hinano Kanagawa;Chiharu Ozakai;Taichi Nishimura;Hayato Tokuda;Tetsuto Tsunoda;Hiroto Kaku

文献摘要

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本文报道了在芳族聚酮衍生的蚜虫色素中发现的吡喃萘醌衍生物的立体选择性合成。这种方法的特点是苯酞与碳水化合物衍生的光学活性烯酮的阴离子[4+2]-成环。另外的合成步骤提供了获得尿白蛋白酶和绿蛋白酶的单体片段的途径。还研究了带有磺酰基或氰基的苯酞的简便制备的优化。
A stereoselective synthesis of a pyranonaphthoquinone derivative found in aromatic polyketide-derived aphid pigments is reported herein. This approach features the anionic [4+2]-annulation of phthalides with a carbohydrate-derived optically active enone. Additional synthetic steps provide access to the monomer fragment of uroleuconaphins and viridaphins. The optimization for a facile preparation of phthalides bearing sulfonyl or cyano groups are also studied.