89461-82-5

Upstream product

• 20780-54-5 (S)-styrene oxide 
• 98607-38-6 5-[(3aS,4R,5R,6aS)-5-Hydroxy-4-mercapto-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid 
• 89461-78-9 (3aS,4R,5R,6aR)-5-Hydroxy-4-((S)-2-hydroxy-2-phenyl-ethylsulfanyl)-hexahydro-pentalen-2-one 
• 88224-55-9 5-[(3aS,4R,5R,6aS)-5-Hydroxy-4-((S)-2-hydroxy-2-phenyl-ethylsulfanyl)-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 

Relevant academic research and scientific papers

EINE BEQUEME UND VIELSEITIGE SYNTHESE VON 13-THIA-CARBACYCLINEN

A versatile and convenient large scale synthesis of 13-thiacarbacyclins is reported.

An eight synthesis of an orally active antihypertensive carba-prostacyclin analog

A short synthesis of carbacyclin analog 1 (code no. EMD 46 335) starting from cyclopentadiene is described, with on overall yield of better than 5%. There is a need for a prostacyclin analog that is stable both chemically and metabolically. Chemical stability can be achieved by replacing to oxygen atom of the enolether function by a carbon atom (→ carbacyclin). Metabolical stability can - for instance - be enhanced by adding a substituent to the C15 or C16 carbon atom. To proceed on this line: since PGI3 is more active than PGI2, replacement of the C16-20-n-pentyl chain by a phenyl group should furthermore result in an enhancement of activity. Replacement of the C13-14-vinyl moiety by a S-CH2-link was thought to provide compounds more convenient to synthesize. We also were interested in designing a prodrug to the active part that does not only give rise to an enhanced shelf stability but also was to facilitate purification (i.e. 5 E,Z-separation) on the last step of its synthesis. On the other hand, it had to be labil enough to readily be activated in vivo and in vitro.