Stereoselective routes to aryl substituted gamma-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids

Macabeo, Allan Patrick G. and Kreuzer, Andreas and Reiser, Oliver (2011) Stereoselective routes to aryl substituted gamma-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids. ORGANIC & BIOMOLECULAR CHEMISTRY, 9 (9). pp. 3146-3150. ISSN 1477-0520, 1477-0539

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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.

Item Type: Article
Uncontrolled Keywords: ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ORGANOTITANIUM REAGENTS; NUCLEOPHILIC-ADDITION; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; PARACONIC ACIDS; SINGLET OXYGEN; BIELSCHOWSKYSIN; ORGANOBORANES;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 01 Jul 2020 09:52
Last Modified: 01 Jul 2020 09:52
URI: https://pred.uni-regensburg.de/id/eprint/21645

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