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一种获取水飞蓟宾的仿生策略：(-)-异水飞蓟宾A的全合成。

A biomimetic strategy to access the silybins: total synthesis of (-)-isosilybin A.

作者信息

McDonald Benjamin R, Nibbs Antoinette E, Scheidt Karl A

机构信息

Dept. of Chemistry, Dept. of Pharmacology, Center for Molecular Innovation and Drug Discovery, Northwestern University , 2145 Sheridan Road, Evanston, Illinois 60208, United States.

出版信息

Org Lett. 2015 Jan 2;17(1):98-101. doi: 10.1021/ol503303w. Epub 2014 Dec 17.

DOI:10.1021/ol503303w
PMID:25517432
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4284651/
Abstract

We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

摘要

我们报道了(-)-异水飞蓟宾A的首次不对称全合成。采用一种高度官能化查尔酮的后期催化仿生环化反应来形成特征性的苯并吡喃酮环。一种用于该查尔酮的稳健且灵活的方法为制备水飞蓟宾天然产物的整个异构体家族提供了途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/b0555126845f/ol-2014-03303w_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/eca9149a4f8a/ol-2014-03303w_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/3aa2541b3f1b/ol-2014-03303w_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/43df6a0849d2/ol-2014-03303w_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/b0555126845f/ol-2014-03303w_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/eca9149a4f8a/ol-2014-03303w_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/3aa2541b3f1b/ol-2014-03303w_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/43df6a0849d2/ol-2014-03303w_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ea4/4284651/b0555126845f/ol-2014-03303w_0004.jpg

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