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间苯三酚选择性合成原花青素 B6，一种 4-6 缩合的 (+)-儿茶素二聚体，通过分子内缩合。

Regioselective Synthesis of Procyanidin B6, A 4-6-Condensed (+)-Catechin Dimer, by Intramolecular Condensation.

机构信息

Graduate School of Engineering, Osaka Electro-Communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan.

College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.

出版信息

Molecules. 2018 Jan 18;23(1):205. doi: 10.3390/molecules23010205.

DOI:10.3390/molecules23010205
PMID:29346322
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6017110/
Abstract

Proanthocyanidins, also known as condensed tannins or oligomeric flavonoids, are found in many edible plants and exhibit interesting biological activities. Herein, we report a new, simple method for the stereoselective synthesis of procyanidin B6, a (+)-catechin-(4-6)-(+)-catechin dimer, by Lewis acid-catalyzed intramolecular condensation. The 5---butyldimethylsilyl (TBDMS) group of 5,7,3'4'-tetra--TBDMS-(+)-catechin was regioselectively removed using trifluoroacetic acid, leading to the "regio-controlled" synthesis of procyanidin B6. The 5-hydroxyl group of the 7,3',4'-tri--TBDMS-(+)-catechin nucleophile and the 3-hydroxyl group of 5,7,3',4'-tetra--benzylated-(+)-catechin electrophile were connected with an azelaic acid. The subsequent SnCl₄-catalyzed intramolecular condensation proceeded smoothly to give the 4-6-condensed catechin dimer. This is the first report on the complete regioselective synthesis of a 4-6-connected oligomer without modifying the 8-position.

摘要

原花青素，也称为缩合单宁或低聚类黄酮，存在于许多食用植物中，并表现出有趣的生物活性。在此，我们报道了一种新的、简单的路易斯酸催化的分子内缩合方法，用于立体选择性合成原花青素 B6，即（+）-儿茶素-（4-6）-（+）-儿茶素二聚体。5---叔丁基二甲基甲硅烷基（TBDMS）基团的 5,7,3'4'-四--TBDMS-（+）-儿茶素通过三氟乙酸进行区域选择性去除，导致原花青素 B6 的“区域控制”合成。7,3',4'-三--TBDMS-（+）-儿茶素亲核试剂的 5-羟基和 5,7,3',4'-四--苄基-（+）-儿茶素的 3-羟基通过壬二酸连接。随后 SnCl4 催化的分子内缩合顺利进行，得到了 4-6-缩合的儿茶素二聚体。这是第一个关于在不修饰 8-位的情况下完全区域选择性合成 4-6 连接低聚物的报道。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/858a51ecdc1b/molecules-23-00205-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/64d22e4ca97d/molecules-23-00205-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/c5bba4fec516/molecules-23-00205-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/41cf0c630b9a/molecules-23-00205-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/d32564a027a2/molecules-23-00205-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/e6b39054e195/molecules-23-00205-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/858a51ecdc1b/molecules-23-00205-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/64d22e4ca97d/molecules-23-00205-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/c5bba4fec516/molecules-23-00205-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/41cf0c630b9a/molecules-23-00205-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/d32564a027a2/molecules-23-00205-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/e6b39054e195/molecules-23-00205-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aeae/6017110/858a51ecdc1b/molecules-23-00205-sch004.jpg

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