High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments

We have developed a powerful concept for the rapid assembly of a series of twenty‐four homochiral building blocks from simple racemic trans‐2,4‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetr...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2000-09, Vol.6 (18), p.3313-3320
Main Authors: Misske, Andrea M., Hoffmann, H. Martin R.
Format: Article
Language:English
Subjects:
aldol reactions
biodiversity
carbohydrate
combinatorial chemistry
polyketides
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 3320
container_issue 18
container_start_page 3313
container_title Chemistry : a European journal
container_volume 6
creator Misske, Andrea M.
Hoffmann, H. Martin R.
description We have developed a powerful concept for the rapid assembly of a series of twenty‐four homochiral building blocks from simple racemic trans‐2,4‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetrades of anomeric carbohydrate mimics, and eight stereotetrades of acyclic polypropionate units. The utility of these enantiopure materials (average 94 % ee) in natural product synthesis is demonstrated and shown to complement the popular aldol method.
doi_str_mv 10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1859339352</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1859339352</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4193-5a6760f9b5499fa8d7cdc5647db08e1b570d1d31b8a036424dd5c87936e6cfba3</originalsourceid><addsrcrecordid>eNqFkcGO0zAQhiMEYsvCKyAfu4cUO46duKCVquzSFrXbFQVx4DByYmdrNk2KnQJ5EN4Xh3bLASF8GXn0z_fb8wdBRvCIYBy9Gq7n2fyCsIiENOFsGGF_BGEXfEzSN5QSOh5P5ldhNrte9rdLOsKjbPU6CvGjYHCaexwMsIiTkDMqzoJnzn3pMZzSp8EZIZgKLxwEP2fmboPWrba6KTZ6awpZoSvzTVtn2g7JWqHJblf5dmua2qGysajdaLTual-ccagp0VJaU2t0I9u99eO3tlH7onVjNEELk1tpu16VSZs3m05Z2Wq0NN7K_ebfNlV3r1ujPFXfbXXduufBk1JWTr841vPg49vrD9ksXKym82yyCIuYCBoyyROOS5GzWIhSpiopVMF4nKgcp5rkLMGKKEryVGLK4yhWihVpIijXvChzSc-D4YG7s83XvXYtbI0rdFXJWjd7ByRlglJBWeSlnw_SwjbOWV3Czpqt_xoQDH1uAH1u0O8f-v3DQ27APQf6pAB8bvCQG1DAkK0gAuzpL48P2edbrf6wj0F5ARwE302lu7-8_2_9D-dTzzuEBwfjWv3j5CDtPfCEJgw-3Uwher9cv8NT4Zm_AC75xfA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1859339352</pqid></control><display><type>article</type><title>High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments</title><source>Wiley</source><creator>Misske, Andrea M. ; Hoffmann, H. Martin R.</creator><creatorcontrib>Misske, Andrea M. ; Hoffmann, H. Martin R.</creatorcontrib><description>We have developed a powerful concept for the rapid assembly of a series of twenty‐four homochiral building blocks from simple racemic trans‐2,4‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetrades of anomeric carbohydrate mimics, and eight stereotetrades of acyclic polypropionate units. The utility of these enantiopure materials (average 94 % ee) in natural product synthesis is demonstrated and shown to complement the popular aldol method.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/(SICI)1521-3765(20000915)6:18&lt;3313::AID-CHEM3313&gt;3.0.CO;2-0</identifier><identifier>PMID: 11039521</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>aldol reactions ; biodiversity ; carbohydrate ; combinatorial chemistry ; polyketides</subject><ispartof>Chemistry : a European journal, 2000-09, Vol.6 (18), p.3313-3320</ispartof><rights>2000 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11039521$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Misske, Andrea M.</creatorcontrib><creatorcontrib>Hoffmann, H. Martin R.</creatorcontrib><title>High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>We have developed a powerful concept for the rapid assembly of a series of twenty‐four homochiral building blocks from simple racemic trans‐2,4‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetrades of anomeric carbohydrate mimics, and eight stereotetrades of acyclic polypropionate units. The utility of these enantiopure materials (average 94 % ee) in natural product synthesis is demonstrated and shown to complement the popular aldol method.</description><subject>aldol reactions</subject><subject>biodiversity</subject><subject>carbohydrate</subject><subject>combinatorial chemistry</subject><subject>polyketides</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqFkcGO0zAQhiMEYsvCKyAfu4cUO46duKCVquzSFrXbFQVx4DByYmdrNk2KnQJ5EN4Xh3bLASF8GXn0z_fb8wdBRvCIYBy9Gq7n2fyCsIiENOFsGGF_BGEXfEzSN5QSOh5P5ldhNrte9rdLOsKjbPU6CvGjYHCaexwMsIiTkDMqzoJnzn3pMZzSp8EZIZgKLxwEP2fmboPWrba6KTZ6awpZoSvzTVtn2g7JWqHJblf5dmua2qGysajdaLTual-ccagp0VJaU2t0I9u99eO3tlH7onVjNEELk1tpu16VSZs3m05Z2Wq0NN7K_ebfNlV3r1ujPFXfbXXduufBk1JWTr841vPg49vrD9ksXKym82yyCIuYCBoyyROOS5GzWIhSpiopVMF4nKgcp5rkLMGKKEryVGLK4yhWihVpIijXvChzSc-D4YG7s83XvXYtbI0rdFXJWjd7ByRlglJBWeSlnw_SwjbOWV3Czpqt_xoQDH1uAH1u0O8f-v3DQ27APQf6pAB8bvCQG1DAkK0gAuzpL48P2edbrf6wj0F5ARwE302lu7-8_2_9D-dTzzuEBwfjWv3j5CDtPfCEJgw-3Uwher9cv8NT4Zm_AC75xfA</recordid><startdate>20000915</startdate><enddate>20000915</enddate><creator>Misske, Andrea M.</creator><creator>Hoffmann, H. Martin R.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20000915</creationdate><title>High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments</title><author>Misske, Andrea M. ; Hoffmann, H. Martin R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4193-5a6760f9b5499fa8d7cdc5647db08e1b570d1d31b8a036424dd5c87936e6cfba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>aldol reactions</topic><topic>biodiversity</topic><topic>carbohydrate</topic><topic>combinatorial chemistry</topic><topic>polyketides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Misske, Andrea M.</creatorcontrib><creatorcontrib>Hoffmann, H. Martin R.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Misske, Andrea M.</au><au>Hoffmann, H. Martin R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2000-09-15</date><risdate>2000</risdate><volume>6</volume><issue>18</issue><spage>3313</spage><epage>3320</epage><pages>3313-3320</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>We have developed a powerful concept for the rapid assembly of a series of twenty‐four homochiral building blocks from simple racemic trans‐2,4‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetrades of anomeric carbohydrate mimics, and eight stereotetrades of acyclic polypropionate units. The utility of these enantiopure materials (average 94 % ee) in natural product synthesis is demonstrated and shown to complement the popular aldol method.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>11039521</pmid><doi>10.1002/(SICI)1521-3765(20000915)6:18&lt;3313::AID-CHEM3313&gt;3.0.CO;2-0</doi><tpages>8</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0947-6539
ispartof Chemistry : a European journal, 2000-09, Vol.6 (18), p.3313-3320
issn 0947-6539
1521-3765
language eng
recordid cdi_proquest_miscellaneous_1859339352
source Wiley
subjects aldol reactions
biodiversity
carbohydrate
combinatorial chemistry
polyketides
title High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T01%3A48%3A45IST&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=High%20Stereochemical%20Diversity%20and%20Applications%20for%20the%20Synthesis%20of%20Marine%20Natural%20Products:%20A%20Library%20of%20Carbohydrate%20Mimics%20and%20Polyketide%20Segments&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Misske,%20Andrea%20M.&rft.date=2000-09-15&rft.volume=6&rft.issue=18&rft.spage=3313&rft.epage=3320&rft.pages=3313-3320&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/(SICI)1521-3765(20000915)6:18%3C3313::AID-CHEM3313%3E3.0.CO;2-0&rft_dat=%3Cproquest_cross%3E1859339352%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c4193-5a6760f9b5499fa8d7cdc5647db08e1b570d1d31b8a036424dd5c87936e6cfba3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1859339352&rft_id=info:pmid/11039521&rfr_iscdi=true