Arisetti, Nanaji and Reiser, Oliver (2015) Traceless Stereoinduction for the Enantiopure Synthesis of Substituted-2-Cyclopentenones. ORGANIC LETTERS, 17 (1). pp. 94-97. ISSN 1523-7060, 1523-7052
Full text not available from this repository. (Request a copy)Abstract
The pseudoenantiomeric 4-O-Boc- and 4-OPMP-cyclopent-2-enones, readily available from hydroxymethylenefurane on multigram scale, are demonstrated to be exceptional building blocks for the synthesis of enantiopure 4-alkyl-5-(1'-hydroxyalkyl) substituted 2-cyclopentenones and derivatives thereof. The 4-OR substituent acts as a traceless stereoinducing element, conferring not only 1,2- but also 1,4-stereocontrol with excellent selectivity. The methodology developed here was applied for the rapid synthesis of natural products and biologically active 2-cyclopentenones such as TEI-9826, guaianes, and pseudoguaianolides.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CYCLOPENTENONE PROSTAGLANDIN ANALOGS; 3-COMPONENT COUPLING PROCESS; RING-CLOSING METATHESIS; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ANTITUMOR-ACTIVITY; ALLYLIC SUBSTITUTION; LIPID MICROSPHERES; IN-VIVO; |
| 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: | 25 Jul 2019 12:59 |
| Last Modified: | 25 Jul 2019 12:59 |
| URI: | https://pred.uni-regensburg.de/id/eprint/6118 |
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