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Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids
Macabeo, Allan Patrick, Kreuzer, Andreas and Reiser, Oliver
(2011)
Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids.
Organic & Biomolecular Chemistry 9, pp. 3146-3150.
Date of publication of this fulltext: 25 Jul 2016 10:38
Article
DOI to cite this document: 10.5283/epub.34118
Abstract
Titanium chelate addition of aryl nucleophiles to cyclopropyl aldehyde 6 followed by a tin-catalyzed one-pot retro-aldol, acetalisation and lactonisation sequence afforded cis and trans gamma-aryllactone acetals. A gamma-furyllactone derived by this approach was further transformed in two steps to model compounds for the oxidised northeastern sectors of selected Pseudopterogorgia diterpenoids.
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| Item type | Article | ||||
| Journal or Publication Title | Organic & Biomolecular Chemistry | ||||
| Publisher: | ROYAL SOC CHEMISTRY | ||||
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| Place of Publication: | CAMBRIDGE | ||||
| Volume: | 9 | ||||
| Page Range: | pp. 3146-3150 | ||||
| Date | 2011 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser | ||||
| Identification Number |
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| Keywords | ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ORGANOTITANIUM REAGENTS; NUCLEOPHILIC-ADDITION; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; PARACONIC ACIDS; SINGLET OXYGEN; BIELSCHOWSKYSIN; ORGANOBORANES; | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Yes | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-341184 | ||||
| Item ID | 34118 |
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