Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Analuisa Nava
  • Lukas Trippe
  • Andrea Frank
  • Lars Andernach
  • Till Opatz
  • Udo Nubbemeyer
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000572391900002&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1055/s-0040-1707282
eISSN
1437-2096
Externe Identifier
  • Clarivate Analytics Document Solution ID: PF6WX
ISSN
0936-5214
Ausgabe der Veröffentlichung
01
Zeitschrift
SYNLETT
Schlüsselwörter
  • lipoxin analogue
  • cycloheptatriene
  • electrophilic acylation
  • enantioselective reduction
  • chiral HPLC
  • ECD analysis
Paginierung
45 - 50
Datum der Veröffentlichung
2021
Status
Published
Titel
Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB<sub>4</sub>
Sub types
  • Article
Ausgabe der Zeitschrift
32

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Abstract
<jats:title>Abstract</jats:title><jats:p>Starting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to &gt;99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.</jats:p>
Autoren
  • Udo Nubbemeyer
  • Analuisa Nava
  • Lukas Trippe
  • Andrea Frank
  • Lars Andernach
  • Till Opatz
DOI
10.1055/s-0040-1707282
eISSN
1437-2096
ISSN
0936-5214
Ausgabe der Veröffentlichung
01
Zeitschrift
Synlett
Sprache
en
Online publication date
2020
Paginierung
45 - 50
Datum der Veröffentlichung
2021
Status
Published
Herausgeber
Georg Thieme Verlag KG
Herausgeber URL
http://dx.doi.org/10.1055/s-0040-1707282
Datum der Datenerfassung
2020
Titel
Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4
Ausgabe der Zeitschrift
32

Datenquelle: Crossref

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