Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds

Oligomeric proanthocyanidins (OPCs) have a variety of biological functions, but the formation of 4,8-interflavan bonds faces scaling-up difficulties due to the challenging control of stereoselectivity and the degree of polymerization. Here we report a process to produce procyanidin B3 (1) by mainly...

Full description

Saved in:
Bibliographic Details
Published in:Organic process research & development 2024-07, Vol.28 (7), p.2958-2971
Main Authors: Zhang, Heyanhao, He, Jintao, Cheng, Rongqian, Yan, Huanren, Tang, Mei-Lin, Chang, Jun
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-a163t-4045fd129503c9b6ac2f92d702c23f0763dc8e31091b05aab3b266bead16cc073
container_end_page 2971
container_issue 7
container_start_page 2958
container_title Organic process research & development
container_volume 28
creator Zhang, Heyanhao
He, Jintao
Cheng, Rongqian
Yan, Huanren
Tang, Mei-Lin
Chang, Jun
description Oligomeric proanthocyanidins (OPCs) have a variety of biological functions, but the formation of 4,8-interflavan bonds faces scaling-up difficulties due to the challenging control of stereoselectivity and the degree of polymerization. Here we report a process to produce procyanidin B3 (1) by mainly optimizing the condensation reaction and improving benzylation, C4 activation, and one-pot hydrogenolysis reactions. In an optimized seven-step process, the product 1 was achieved by only one-step chromatography in the case of poor crystallinity of polyphenols. This strategy provided effective access to the stereoselective synthesis of the title compound and other C4–C8 connected OPCs.
doi_str_mv 10.1021/acs.oprd.4c00271
format article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_oprd_4c00271</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c592527043</sourcerecordid><originalsourceid>FETCH-LOGICAL-a163t-4045fd129503c9b6ac2f92d702c23f0763dc8e31091b05aab3b266bead16cc073</originalsourceid><addsrcrecordid>eNp1kEtLw0AUhQdRsFb3LvMDmnpnJpkk7rTYWihUqIK7cDMPTUkyYSYKdekvd2qLO1f3cc49XD5CrilMKTB6g9JPbe_UNJEALKMnZERTBnGai9fT0EPOY0EFnJML77cAkArKRuR73Q91W3_hUNsuMtZFw7uOnpzu0R121oTRyh12taq76J7fRpshaPpt9-tfOGzjjcRGR9ipoGmnrdeNlkP9qaO5de1fUDLJ42UXHKbBTwxhtlP-kpwZbLy-OtYxeZk_PM8e49V6sZzdrWKkgg9xAklqFGVFClwWlUDJTMFUBkwybiATXMlccwoFrSBFrHjFhKg0KiqkhIyPCRxypbPeO23K3tUtul1JodwzLAPDcs-wPDIMJ5PDyV7Z2g_XhQf_t_8ABJ13Mw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Zhang, Heyanhao ; He, Jintao ; Cheng, Rongqian ; Yan, Huanren ; Tang, Mei-Lin ; Chang, Jun</creator><creatorcontrib>Zhang, Heyanhao ; He, Jintao ; Cheng, Rongqian ; Yan, Huanren ; Tang, Mei-Lin ; Chang, Jun</creatorcontrib><description>Oligomeric proanthocyanidins (OPCs) have a variety of biological functions, but the formation of 4,8-interflavan bonds faces scaling-up difficulties due to the challenging control of stereoselectivity and the degree of polymerization. Here we report a process to produce procyanidin B3 (1) by mainly optimizing the condensation reaction and improving benzylation, C4 activation, and one-pot hydrogenolysis reactions. In an optimized seven-step process, the product 1 was achieved by only one-step chromatography in the case of poor crystallinity of polyphenols. This strategy provided effective access to the stereoselective synthesis of the title compound and other C4–C8 connected OPCs.</description><identifier>ISSN: 1083-6160</identifier><identifier>EISSN: 1520-586X</identifier><identifier>DOI: 10.1021/acs.oprd.4c00271</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic process research &amp; development, 2024-07, Vol.28 (7), p.2958-2971</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a163t-4045fd129503c9b6ac2f92d702c23f0763dc8e31091b05aab3b266bead16cc073</cites><orcidid>0000-0001-6481-7130</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Zhang, Heyanhao</creatorcontrib><creatorcontrib>He, Jintao</creatorcontrib><creatorcontrib>Cheng, Rongqian</creatorcontrib><creatorcontrib>Yan, Huanren</creatorcontrib><creatorcontrib>Tang, Mei-Lin</creatorcontrib><creatorcontrib>Chang, Jun</creatorcontrib><title>Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds</title><title>Organic process research &amp; development</title><addtitle>Org. Process Res. Dev</addtitle><description>Oligomeric proanthocyanidins (OPCs) have a variety of biological functions, but the formation of 4,8-interflavan bonds faces scaling-up difficulties due to the challenging control of stereoselectivity and the degree of polymerization. Here we report a process to produce procyanidin B3 (1) by mainly optimizing the condensation reaction and improving benzylation, C4 activation, and one-pot hydrogenolysis reactions. In an optimized seven-step process, the product 1 was achieved by only one-step chromatography in the case of poor crystallinity of polyphenols. This strategy provided effective access to the stereoselective synthesis of the title compound and other C4–C8 connected OPCs.</description><issn>1083-6160</issn><issn>1520-586X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kEtLw0AUhQdRsFb3LvMDmnpnJpkk7rTYWihUqIK7cDMPTUkyYSYKdekvd2qLO1f3cc49XD5CrilMKTB6g9JPbe_UNJEALKMnZERTBnGai9fT0EPOY0EFnJML77cAkArKRuR73Q91W3_hUNsuMtZFw7uOnpzu0R121oTRyh12taq76J7fRpshaPpt9-tfOGzjjcRGR9ipoGmnrdeNlkP9qaO5de1fUDLJ42UXHKbBTwxhtlP-kpwZbLy-OtYxeZk_PM8e49V6sZzdrWKkgg9xAklqFGVFClwWlUDJTMFUBkwybiATXMlccwoFrSBFrHjFhKg0KiqkhIyPCRxypbPeO23K3tUtul1JodwzLAPDcs-wPDIMJ5PDyV7Z2g_XhQf_t_8ABJ13Mw</recordid><startdate>20240719</startdate><enddate>20240719</enddate><creator>Zhang, Heyanhao</creator><creator>He, Jintao</creator><creator>Cheng, Rongqian</creator><creator>Yan, Huanren</creator><creator>Tang, Mei-Lin</creator><creator>Chang, Jun</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6481-7130</orcidid></search><sort><creationdate>20240719</creationdate><title>Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds</title><author>Zhang, Heyanhao ; He, Jintao ; Cheng, Rongqian ; Yan, Huanren ; Tang, Mei-Lin ; Chang, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a163t-4045fd129503c9b6ac2f92d702c23f0763dc8e31091b05aab3b266bead16cc073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Heyanhao</creatorcontrib><creatorcontrib>He, Jintao</creatorcontrib><creatorcontrib>Cheng, Rongqian</creatorcontrib><creatorcontrib>Yan, Huanren</creatorcontrib><creatorcontrib>Tang, Mei-Lin</creatorcontrib><creatorcontrib>Chang, Jun</creatorcontrib><collection>CrossRef</collection><jtitle>Organic process research &amp; development</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Heyanhao</au><au>He, Jintao</au><au>Cheng, Rongqian</au><au>Yan, Huanren</au><au>Tang, Mei-Lin</au><au>Chang, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds</atitle><jtitle>Organic process research &amp; development</jtitle><addtitle>Org. Process Res. Dev</addtitle><date>2024-07-19</date><risdate>2024</risdate><volume>28</volume><issue>7</issue><spage>2958</spage><epage>2971</epage><pages>2958-2971</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><abstract>Oligomeric proanthocyanidins (OPCs) have a variety of biological functions, but the formation of 4,8-interflavan bonds faces scaling-up difficulties due to the challenging control of stereoselectivity and the degree of polymerization. Here we report a process to produce procyanidin B3 (1) by mainly optimizing the condensation reaction and improving benzylation, C4 activation, and one-pot hydrogenolysis reactions. In an optimized seven-step process, the product 1 was achieved by only one-step chromatography in the case of poor crystallinity of polyphenols. This strategy provided effective access to the stereoselective synthesis of the title compound and other C4–C8 connected OPCs.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.oprd.4c00271</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0001-6481-7130</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1083-6160
ispartof Organic process research & development, 2024-07, Vol.28 (7), p.2958-2971
issn 1083-6160
1520-586X
language eng
recordid cdi_crossref_primary_10_1021_acs_oprd_4c00271
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Optimization for the Preparation of Procyanidin B3: Strategy for Gram-Scale and Stereoselective Formation of 4,8-Interflavan Bonds
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-13T02%3A10%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Optimization%20for%20the%20Preparation%20of%20Procyanidin%20B3:%20Strategy%20for%20Gram-Scale%20and%20Stereoselective%20Formation%20of%204,8-Interflavan%20Bonds&rft.jtitle=Organic%20process%20research%20&%20development&rft.au=Zhang,%20Heyanhao&rft.date=2024-07-19&rft.volume=28&rft.issue=7&rft.spage=2958&rft.epage=2971&rft.pages=2958-2971&rft.issn=1083-6160&rft.eissn=1520-586X&rft_id=info:doi/10.1021/acs.oprd.4c00271&rft_dat=%3Cacs_cross%3Ec592527043%3C/acs_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a163t-4045fd129503c9b6ac2f92d702c23f0763dc8e31091b05aab3b266bead16cc073%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true