Zur asymmetrischen Synthese von C-Azanucleosiden und 2-Amino-1,3-diolen

The first part of the thesis investigates the asymmetric synthesis of C-Azanucleosides. The different approaches envisaged, using the SAMP- /RAMP-Hydrazone methodology to synthesese the desired compound are herein described. Several chiral building blocks were synthesized in high diastereomeric and enantiomeric excess however the titled compound could not be obtained. In the second part a diastereo- and enantioselective synthesis of various 2-amino-1,3-diols (de>=96%, ee = 90-94%) is presented. Starting from the Dioxanon-SAMP-Hydrazone, the anti-configured acetonid protected products were obtained in a six-step procedure. The stereogenic centres were generated by a diastereoselective alpha-alkylation with various electrophiles and subsequent diastereoselektive reduction of the ketone. The desired amines, were obtained by conversion of the hydroxyl functionality into an azide, and subsequent reduction. After removal of the acetonid protecting group the ammonium salt of the 2-amino-1,3-diols could be isolated. Using the methodology previously developed, the ammonium salt of D-erythro-sphinganine was synthesized starting from the Dioxanone-RAMP-hydrazone in a seven-step procedure. The desired product was obtained in 47% overall yield, with excellent diastereo- and enatiomeric excess (de, ee>=96%).

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2003

Author dc:creator

• Müller-Hüwen, Anke

Contributors dc:contributor

• Enders, Dieter

• info:eu-repo/classification/ddc/540
• Chemie
• Hydrazone
• alpha-Alkylierung
• Asymmetrische Synthese
• Aminodiole

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-121022%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:59216