A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B

Abstract The transition-metal-free total syntheses of the oxygenated carbazole natural products glycoborine, carbazomycin A and carbazomycin B are reported. The key step involves an NBS-mediated cyclobutanol ring expansion to 4-tetralones for the preparation of the tricyclic carbazole core.

Saved in:
Bibliographic Details
Published in:Synlett 2023-05, Vol.34 (8), p.937-942
Main Authors: Natho, Philipp, Allen, Lewis A. T., Parsons, Philip J.
Format: Article
Language:English
Subjects:
letter
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-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3
cites cdi_FETCH-LOGICAL-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3
container_end_page 942
container_issue 8
container_start_page 937
container_title Synlett
container_volume 34
creator Natho, Philipp
Allen, Lewis A. T.
Parsons, Philip J.
description Abstract The transition-metal-free total syntheses of the oxygenated carbazole natural products glycoborine, carbazomycin A and carbazomycin B are reported. The key step involves an NBS-mediated cyclobutanol ring expansion to 4-tetralones for the preparation of the tricyclic carbazole core.
doi_str_mv 10.1055/s-0042-1751411
format article
fullrecord <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_0042_1751411</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_0042_1751411</sourcerecordid><originalsourceid>FETCH-LOGICAL-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3</originalsourceid><addsrcrecordid>eNp1kEFLwzAYhoMoOKdXz_kBZuZrk7T1NsucwmCg81zSNN0yuqQkHawe_eV2bB48ePrg5XlfPh6E7oFOgHL-GAilLCKQcGAAF2gELE5IRDNxiUY0iwXhEbBrdBPCllJgaUZH6HuK8141rtx30roGvxu7JrNDK20wzuJp23on1QZ3Di8P_Vpb2ekK59KX8ss1Ojzhletkgz962210MAG7Gs-bXrnSeWP1wy-765UZ9rC01d_o-RZd1bIJ-u58x-jzZbbKX8liOX_LpwuiYkg6IrJalykDGkkJScmSTNe1zATltII6SpUWoNM0LnnMKdNCQUUFF4MLyWEg4zGanHaVdyF4XRetNzvp-wJocTRYhOJosDgbHArkVOg2Ru90sXV7b4cP_-N_ALL-cyM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B</title><source>Thieme Connect Journals</source><creator>Natho, Philipp ; Allen, Lewis A. T. ; Parsons, Philip J.</creator><creatorcontrib>Natho, Philipp ; Allen, Lewis A. T. ; Parsons, Philip J.</creatorcontrib><description>Abstract The transition-metal-free total syntheses of the oxygenated carbazole natural products glycoborine, carbazomycin A and carbazomycin B are reported. The key step involves an NBS-mediated cyclobutanol ring expansion to 4-tetralones for the preparation of the tricyclic carbazole core.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-0042-1751411</identifier><language>eng</language><publisher>Rüdigerstraße 14, 70469 Stuttgart, Germany: Georg Thieme Verlag KG</publisher><subject>letter</subject><ispartof>Synlett, 2023-05, Vol.34 (8), p.937-942</ispartof><rights>This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3</citedby><cites>FETCH-LOGICAL-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3</cites><orcidid>0000-0002-3419-0848 ; 0000-0002-9158-4034 ; 0000-0002-4525-2469</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0042-1751411.pdf$$EPDF$$P50$$Gthieme$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0042-1751411$$EHTML$$P50$$Gthieme$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,3004,3005,27898,27899,54531,54532</link.rule.ids></links><search><creatorcontrib>Natho, Philipp</creatorcontrib><creatorcontrib>Allen, Lewis A. T.</creatorcontrib><creatorcontrib>Parsons, Philip J.</creatorcontrib><title>A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B</title><title>Synlett</title><addtitle>Synlett</addtitle><description>Abstract The transition-metal-free total syntheses of the oxygenated carbazole natural products glycoborine, carbazomycin A and carbazomycin B are reported. The key step involves an NBS-mediated cyclobutanol ring expansion to 4-tetralones for the preparation of the tricyclic carbazole core.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>0U6</sourceid><recordid>eNp1kEFLwzAYhoMoOKdXz_kBZuZrk7T1NsucwmCg81zSNN0yuqQkHawe_eV2bB48ePrg5XlfPh6E7oFOgHL-GAilLCKQcGAAF2gELE5IRDNxiUY0iwXhEbBrdBPCllJgaUZH6HuK8141rtx30roGvxu7JrNDK20wzuJp23on1QZ3Di8P_Vpb2ekK59KX8ss1Ojzhletkgz962210MAG7Gs-bXrnSeWP1wy-765UZ9rC01d_o-RZd1bIJ-u58x-jzZbbKX8liOX_LpwuiYkg6IrJalykDGkkJScmSTNe1zATltII6SpUWoNM0LnnMKdNCQUUFF4MLyWEg4zGanHaVdyF4XRetNzvp-wJocTRYhOJosDgbHArkVOg2Ru90sXV7b4cP_-N_ALL-cyM</recordid><startdate>20230512</startdate><enddate>20230512</enddate><creator>Natho, Philipp</creator><creator>Allen, Lewis A. T.</creator><creator>Parsons, Philip J.</creator><general>Georg Thieme Verlag KG</general><scope>0U6</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3419-0848</orcidid><orcidid>https://orcid.org/0000-0002-9158-4034</orcidid><orcidid>https://orcid.org/0000-0002-4525-2469</orcidid></search><sort><creationdate>20230512</creationdate><title>A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B</title><author>Natho, Philipp ; Allen, Lewis A. T. ; Parsons, Philip J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Natho, Philipp</creatorcontrib><creatorcontrib>Allen, Lewis A. T.</creatorcontrib><creatorcontrib>Parsons, Philip J.</creatorcontrib><collection>Thieme Connect Journals Open Access</collection><collection>CrossRef</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Natho, Philipp</au><au>Allen, Lewis A. T.</au><au>Parsons, Philip J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2023-05-12</date><risdate>2023</risdate><volume>34</volume><issue>8</issue><spage>937</spage><epage>942</epage><pages>937-942</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>Abstract The transition-metal-free total syntheses of the oxygenated carbazole natural products glycoborine, carbazomycin A and carbazomycin B are reported. The key step involves an NBS-mediated cyclobutanol ring expansion to 4-tetralones for the preparation of the tricyclic carbazole core.</abstract><cop>Rüdigerstraße 14, 70469 Stuttgart, Germany</cop><pub>Georg Thieme Verlag KG</pub><doi>10.1055/s-0042-1751411</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3419-0848</orcidid><orcidid>https://orcid.org/0000-0002-9158-4034</orcidid><orcidid>https://orcid.org/0000-0002-4525-2469</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0936-5214
ispartof Synlett, 2023-05, Vol.34 (8), p.937-942
issn 0936-5214
1437-2096
language eng
recordid cdi_crossref_primary_10_1055_s_0042_1751411
source Thieme Connect Journals
subjects letter
title A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-27T04%3A30%3A36IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Cyclobutanol%20Ring-Expansion%20Approach%20to%20Oxygenated%20Carbazoles:%20Total%20Synthesis%20of%20Glycoborine,%20Carbazomycin%20A%20and%20Carbazomycin%20B&rft.jtitle=Synlett&rft.au=Natho,%20Philipp&rft.date=2023-05-12&rft.volume=34&rft.issue=8&rft.spage=937&rft.epage=942&rft.pages=937-942&rft.issn=0936-5214&rft.eissn=1437-2096&rft_id=info:doi/10.1055/s-0042-1751411&rft_dat=%3Cthieme_cross%3E10_1055_s_0042_1751411%3C/thieme_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c317t-69feb84102aa17b479effa96050d1f28ce61e883b53504e6c1d0656141a51ffa3%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