73712-08-0

Upstream product

• 73691-57-3 9-deoxy-9,10-dehydro-15-t-butyldimethylsilyloxyprostaglandin D₂ 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 72974-55-1 <5-<3'-(dimethyl-t-butylsilyloxy)oct-1'-enyl>-4-hydroxycyclopent-2-enyl>acetaldehyde 
• 76759-24-5 4-exo-(3'-t-butyldimethylsilyloxyoct-1'-enyl)-6-endo-hydroxymethylbicyclo<3.1.0>hex-2-ene 
• 72974-56-2 9-deoxa-9,10-dehydro-15-t-butyldimethylsilyloxyprostaglandin F₂α 
• 72974-53-9 4-exo-(3'-t-butyldimethylsilyloxyoct-1'-enyl)bicyclo<3.1.0>hex-2-ene-6-carboxylic acid 
• 72974-55-1 2-<4'-endo-hydroxy-5'-exo-(3''-t-butyldimethylsilyloxyoct-1''-enyl)cyclopent-2'-enyl>acetaldehyde 
• 75758-78-0 4-exo-(3'-t-butyldimethylsilyloxyoct-1'-enyl)bicyclo<3.1.0>hex-2-ene-6-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of optically active prostaglandin-J2 and 15-deoxy-δ12,14-prostaglandin-J2

An efficient route to optically pure prostaglandin-J2 compounds has been discovered: ent-PGJ2 is shown to display antiviral activity against Sendai virus with a similar potency to the natural enantiomer.

Preparation and some reactions of 2-oxatricyclo[3.3.0.04,6]oct- 7-en-3-one: Synthesis of 9-deoxa-9,10-dehydroprostaglandin D2

The tricyclic lactone (1) was prepared by two methods. Reaction of (1) with electrophilic reagents occurred on the more exposed exo-face of the alkene unit resulting in the formation of the epoxylactone (8) on peracid oxidation and the bromolactones (9)-(11) on bromination in the appropriate solvent. Thiophenoxide ion reacted with (1) in SN2 fashion to give the acid (13) while deuteriation studies suggested that lithium dibutylcuprate reacted with (1) through the SN′ pathway preferentially to give the acid (15). The cuprate reagent (20) reacted with the lactone (1) to form the acid (21) which was converted into the prostanoid (29) in a standard fashion.