A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine

We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2004-06, Vol.69 (13), p.4548-4550
Main Authors: Luo, Shengjun, Zhao, Jingrui, Zhai, Hongbin
Format: Article
Language:English
Subjects:
Carbolines - chemical synthesis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Structure
Organic chemistry
Preparations and properties
Quinolizines - chemical synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363
cites cdi_FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363
container_end_page 4550
container_issue 13
container_start_page 4548
container_title Journal of organic chemistry
container_volume 69
creator Luo, Shengjun
Zhao, Jingrui
Zhai, Hongbin
description We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal synthesis of β-carboline alkaloid (±)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids.
doi_str_mv 10.1021/jo049459s
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_66645809</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>66645809</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363</originalsourceid><addsrcrecordid>eNptkU9v0zAYxiMEYmVw4AsgX0BMEObEcf5wCxXdJk2iqOVUVdEb-83wcOzOTiTaE0e48k34Cpz4HPskpLRsHPDFh-ennx_5CYLHEX0V0Tg6vrQ0KRJe-DvBKOIxDdOCJneDEaVxHLI4ZQfBA-8v6XA45_eDgy0UF1ExCn6VZAK-I6X32NZ6TWxDpmg6EGuhlSBv0GwWzVIZabVdxC9ZCMurXhmr1UZJZZCMrUNSr8kcjMSWnJkOXWs1il6DIxPrWtCk3EC4YOQFYUsyHswWpFSdsuZ4qkSH3fXX77MVmguN7k-uNrBNX19_-UbKv5LZ2nQf0Su_Lfn854-jcHjzou-sG3o8DO41oD0-2t-HwYfJ2_n4NDx_d3I2Ls9DYFnRhWnDmyIRTSYhElTUGHOgOdA0yZuIQyJpUTOEjEa1zAWrG0njBnOWc5lhwlJ2GDzbeVfOXvXou6pVXqDWYND2vkrTNOE5LQbwaAcKZ7132FQrp1pw6yqi1Xa26ma2gX2yl_Z1i_KW3O80AE_3AHgBunFghPL_cHmeRowOXLjjlO_w800O7lOVZizj1Xw6q5Lx5HRyMn1fxbdeEH7o0zsz_N1_Cv4GNMfAHQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>66645809</pqid></control><display><type>article</type><title>A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Luo, Shengjun ; Zhao, Jingrui ; Zhai, Hongbin</creator><creatorcontrib>Luo, Shengjun ; Zhao, Jingrui ; Zhai, Hongbin</creatorcontrib><description>We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal synthesis of β-carboline alkaloid (±)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo049459s</identifier><identifier>PMID: 15202919</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Carbolines - chemical synthesis ; Chemistry ; Cyclization ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Quinolizines - chemical synthesis</subject><ispartof>Journal of organic chemistry, 2004-06, Vol.69 (13), p.4548-4550</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363</citedby><cites>FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=15886130$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15202919$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Luo, Shengjun</creatorcontrib><creatorcontrib>Zhao, Jingrui</creatorcontrib><creatorcontrib>Zhai, Hongbin</creatorcontrib><title>A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal synthesis of β-carboline alkaloid (±)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids.</description><subject>Carbolines - chemical synthesis</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Quinolizines - chemical synthesis</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptkU9v0zAYxiMEYmVw4AsgX0BMEObEcf5wCxXdJk2iqOVUVdEb-83wcOzOTiTaE0e48k34Cpz4HPskpLRsHPDFh-ennx_5CYLHEX0V0Tg6vrQ0KRJe-DvBKOIxDdOCJneDEaVxHLI4ZQfBA-8v6XA45_eDgy0UF1ExCn6VZAK-I6X32NZ6TWxDpmg6EGuhlSBv0GwWzVIZabVdxC9ZCMurXhmr1UZJZZCMrUNSr8kcjMSWnJkOXWs1il6DIxPrWtCk3EC4YOQFYUsyHswWpFSdsuZ4qkSH3fXX77MVmguN7k-uNrBNX19_-UbKv5LZ2nQf0Su_Lfn854-jcHjzou-sG3o8DO41oD0-2t-HwYfJ2_n4NDx_d3I2Ls9DYFnRhWnDmyIRTSYhElTUGHOgOdA0yZuIQyJpUTOEjEa1zAWrG0njBnOWc5lhwlJ2GDzbeVfOXvXou6pVXqDWYND2vkrTNOE5LQbwaAcKZ7132FQrp1pw6yqi1Xa26ma2gX2yl_Z1i_KW3O80AE_3AHgBunFghPL_cHmeRowOXLjjlO_w800O7lOVZizj1Xw6q5Lx5HRyMn1fxbdeEH7o0zsz_N1_Cv4GNMfAHQ</recordid><startdate>20040625</startdate><enddate>20040625</enddate><creator>Luo, Shengjun</creator><creator>Zhao, Jingrui</creator><creator>Zhai, Hongbin</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040625</creationdate><title>A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine</title><author>Luo, Shengjun ; Zhao, Jingrui ; Zhai, Hongbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Carbolines - chemical synthesis</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Quinolizines - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Shengjun</creatorcontrib><creatorcontrib>Zhao, Jingrui</creatorcontrib><creatorcontrib>Zhai, Hongbin</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Shengjun</au><au>Zhao, Jingrui</au><au>Zhai, Hongbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-06-25</date><risdate>2004</risdate><volume>69</volume><issue>13</issue><spage>4548</spage><epage>4550</epage><pages>4548-4550</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal synthesis of β-carboline alkaloid (±)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15202919</pmid><doi>10.1021/jo049459s</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2004-06, Vol.69 (13), p.4548-4550
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_66645809
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Carbolines - chemical synthesis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Structure
Organic chemistry
Preparations and properties
Quinolizines - chemical synthesis
title A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-23T04%3A36%3A31IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Fast%20Assembly%20of%20Pentacyclic%20Benz%5Bf%5Dindolo%5B2,3-a%5Dquinolizidine%20Core%20by%20Tandem%20Intermolecular%20Formal%20Aza-%5B3%20+%203%5D%20Cycloaddition/Pictet%E2%88%92Spengler%20Cyclization:%E2%80%89%20A%20Formal%20Synthesis%20of%20(%C2%B1)-Tangutorine&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Luo,%20Shengjun&rft.date=2004-06-25&rft.volume=69&rft.issue=13&rft.spage=4548&rft.epage=4550&rft.pages=4548-4550&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo049459s&rft_dat=%3Cproquest_cross%3E66645809%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a379t-6f5f94cf7da1c0cbe25a08a0648f15a4d09b3ea701bd8c3bfd02fe8385d7e4363%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=66645809&rft_id=info:pmid/15202919&rfr_iscdi=true