Asymmetrische organokatalytische de novo Synthese von Kohlenhydraten, Phytosphingosinen und 1-epi-(+)MK7607

Carbohydrates are of enormous importance for chemical, biological and medicinal science, because they play key roles in many biological processes. Furthermore they are used as targets for drug discovery. The synthesis of carbohydrates is often difficult as a consequence of the high density of funtional groups, whereas flexible and efficient synthetic approaches towards carbohydrates are highly desirable.This thesis deals with the development of an asymmetric, organocatalytic and biomimetic [C3+Cn] concept for the direct synthesis of selectively protected carbohydrates and aminosugars. 2,2-dimethyl-1,3-dioxan-5-one, a chemical dihydroxyacetone-equivalent, and different functionalized aldehydes were used in a proline-catalyzed aldol or Mannich reaction to afford the corresponding carbohydrates. These protected sugars can be easily deprotected or used as chrial building blocks. They were employed for the diversity oriented synthesis of aldopentoses and natural product synthesis. This was demonstrated by the synthesis of D-arabino- and L-ribo-phytosphingosine and 1-epi-(+)MK7607.

Grantor dc:publisher

Mainz

Year dc:date

2006

Author dc:creator

• Grondal, Christoph Bernhard

Contributors dc:contributor

• Enders, Dieter

• info:eu-repo/classification/ddc/540
• Chemie

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-122901%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:61223