Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain

The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allyli...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2001-02, Vol.3 (4), p.503-505
Main Authors: Evans, David A, Burch, Jason D
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Cyclopropanes - chemical synthesis
Macrolides
Mannitol - analogs & derivatives
Mannitol - chemistry
Molecular Structure
Stereoisomerism
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-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3
cites cdi_FETCH-LOGICAL-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3
container_end_page 505
container_issue 4
container_start_page 503
container_title Organic letters
container_volume 3
creator Evans, David A
Burch, Jason D
description The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.
doi_str_mv 10.1021/ol0155182
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_70634557</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>70634557</sourcerecordid><originalsourceid>FETCH-LOGICAL-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3</originalsourceid><addsrcrecordid>eNptkD1PwzAQhi0EoqUw8AdQFpAYAr44zsdYRXxJlRhaZst2HerKiYOdDPn3uEpVFm65092jV--9CN0CfgKcwLM1GCiFIjlDc6AJiXNMk_PTnOEZuvJ-jzGETXmJZgCQFwXgOfpa-rFpVO-0jNZj2--U1z6ydRSmqNoZ66wcpbGdsx1vVVzZtue61e13VHFjdKdMb73eqmgZrQ-t2oXzNbqoufHq5tgXaPP6sqne49Xn20e1XMWcAPRxnQPUtFSkzAXHKQ6VFIXIaEqznMtsKzNBgeNCpKUghJQJlhRkQjMlqBJkgR4m2eDuZ1C-Z432UhkTnNrBs_A6SSnNA_g4gdJZ752qWed0w93IALNDhOwUYWDvjqKDaNT2jzxmFoD7CeDSs70dXBte_EfoF3MxdtU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>70634557</pqid></control><display><type>article</type><title>Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Evans, David A ; Burch, Jason D</creator><creatorcontrib>Evans, David A ; Burch, Jason D</creatorcontrib><description>The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0155182</identifier><identifier>PMID: 11178810</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Cyclopropanes - chemical synthesis ; Macrolides ; Mannitol - analogs &amp; derivatives ; Mannitol - chemistry ; Molecular Structure ; Stereoisomerism</subject><ispartof>Organic letters, 2001-02, Vol.3 (4), p.503-505</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3</citedby><cites>FETCH-LOGICAL-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11178810$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Evans, David A</creatorcontrib><creatorcontrib>Burch, Jason D</creatorcontrib><title>Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Cyclopropanes - chemical synthesis</subject><subject>Macrolides</subject><subject>Mannitol - analogs &amp; derivatives</subject><subject>Mannitol - chemistry</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><recordid>eNptkD1PwzAQhi0EoqUw8AdQFpAYAr44zsdYRXxJlRhaZst2HerKiYOdDPn3uEpVFm65092jV--9CN0CfgKcwLM1GCiFIjlDc6AJiXNMk_PTnOEZuvJ-jzGETXmJZgCQFwXgOfpa-rFpVO-0jNZj2--U1z6ydRSmqNoZ66wcpbGdsx1vVVzZtue61e13VHFjdKdMb73eqmgZrQ-t2oXzNbqoufHq5tgXaPP6sqne49Xn20e1XMWcAPRxnQPUtFSkzAXHKQ6VFIXIaEqznMtsKzNBgeNCpKUghJQJlhRkQjMlqBJkgR4m2eDuZ1C-Z432UhkTnNrBs_A6SSnNA_g4gdJZ752qWed0w93IALNDhOwUYWDvjqKDaNT2jzxmFoD7CeDSs70dXBte_EfoF3MxdtU</recordid><startdate>20010222</startdate><enddate>20010222</enddate><creator>Evans, David A</creator><creator>Burch, Jason D</creator><general>American Chemical Society</general><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>20010222</creationdate><title>Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain</title><author>Evans, David A ; Burch, Jason D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Cyclopropanes - chemical synthesis</topic><topic>Macrolides</topic><topic>Mannitol - analogs &amp; derivatives</topic><topic>Mannitol - chemistry</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Evans, David A</creatorcontrib><creatorcontrib>Burch, Jason D</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Evans, David A</au><au>Burch, Jason D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2001-02-22</date><risdate>2001</risdate><volume>3</volume><issue>4</issue><spage>503</spage><epage>505</epage><pages>503-505</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11178810</pmid><doi>10.1021/ol0155182</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2001-02, Vol.3 (4), p.503-505
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_70634557
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Anti-Bacterial Agents - chemical synthesis
Cyclopropanes - chemical synthesis
Macrolides
Mannitol - analogs & derivatives
Mannitol - chemistry
Molecular Structure
Stereoisomerism
title Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T13%3A23%3A03IST&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=Asymmetric%20Synthesis%20of%20the%20Chlorocyclopropane-Containing%20Callipeltoside%20A%20Side%20Chain&rft.jtitle=Organic%20letters&rft.au=Evans,%20David%20A&rft.date=2001-02-22&rft.volume=3&rft.issue=4&rft.spage=503&rft.epage=505&rft.pages=503-505&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0155182&rft_dat=%3Cproquest_cross%3E70634557%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a311t-f711f59e397ba040000288b654567ac6dc6b51a08b49b333920c51c256eb5eb3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=70634557&rft_id=info:pmid/11178810&rfr_iscdi=true