Asymmetrische Synthese von 3-Oxa-15-Deoxy-16-(m-tolyl)-Tetranorisocarbacyclin und 15-Deoxy-16-(m-tolyl)-Tetranorisocarbacyclin

Some years ago besides the known prostacyclin receptor (IP1) a new prostacyclin-specific receptor (IP2) was discovered in the brains of different mammals. Both receptors show different binding-affinities towards stable prostacyclin-analogues. Prostacyclin-analogue 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15-deoxy-TIC) binds with high affinity and selectivity to the IP2-receptor. 15-deoxy-TIC prevents neuronal death in vitro and in vivo and can pass the blood-brain-barrier. Because of these properties 15-deoxy-TIC can possibly be used as a drug against Alzheimers and Parkinsons diseases. This thesis describes the asymmetric total synthesis of the new prostacyclin-analogue 3-oxa-15-deoxy-TIC and a formal total synthesis of the known 15-deoxy-TIC. It is to be expected that under physiological conditions 3-oxa-15-deoxy-TIC is metabolically more stable than 15-deoxy-TIC. The key steps in the syntheses of the target molecules are a conjugate addition of a copperorganyl to an azoalkene and an asymmetric Horner-Wadsworth-Emmons reaction using a chiral phosphonate.

Grantor dc:publisher

Mainz

Year dc:date

2007

Author dc:creator

• van de Sande, Marc

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Chemie
• Asymmetrische Synthese
• Isocarbacyclin
• Prostacyclinanaloga
• 15-Deoxy-TIC
• Medizinische Chemie
• Prostacyclin-Rezeptor
• asymmetric synthesis
• medicinal chemistry
• prostacyclin receptor

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123321%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:61685