140192-36-5

Upstream product

• 140192-35-4 (1R,4R,S,5S)-4-(phenylseleno)-6-(2-pivaloyloxyethyl)-2-oxa-6-azabicyclo<3.3.0>octane-3-one 
• 107319-89-1 (3R)-3-(bromoacetoxy)-1-(2-pivaloyloxyethyl)pyrrolidine-2,5-dione 
• 107319-90-4 (1R)-6-(2-pivaloyloxyethyl)-2-oxa-6-azabicyclo<3.3.0>oct-4-ene-3,7-dione 
• 109755-70-6 (1S,5S)-2-oxa-6-aza-6-(2-(trimethylacetoxy)ethyl)-3-oxobicyclo<3.3.0>octane-7-thione 
• 107319-91-5 (1S,5S)-2-oxa-6-aza-6-(2-(trimethylacetoxy)ethyl)bicyclo<3.3.0>octane-3,7-dione 
• 107319-88-0 (3R)-3-acetoxy-1-(2-acetoxyethyl)pyrrolidine-2,5-dione 
• 109755-67-1 (3R)-3-hydroxy-1-(2-pivaloyloxyethyl)pyrrolidine-2,5-dione 
• 107319-92-6 (1S,5S)-2-oxa-6-aza-6-(2-(trimethylacetoxy)ethyl)bicyclo<3.3.0>octan-3-one 
• 109755-66-0 (3R)-3-hydroxy-1-(2-hydroxyethyl)pyrrolidine-2,5-dione 
• 107319-93-7 (1R,4R,S,5S)-4-(phenylseleno)-6-(2-hydroxyethyl)-2-oxa-6-azabicyclo<3.3.0>octane-3-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 5707-04-0 Phenylselenyl chloride 

Downstream Products

• 130-01-8 (-)-integerrimine 
• 140385-63-3 (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane 
• 85365-61-3 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone 

Relevant academic research and scientific papers

Total Synthesis of Optically Active Integerrimine, a Twelve-membered Dilactonic Pyrrolizidine Alkaloid of Retronecine Type

A total synthesis of the natural enantiomer of integerrimine (1), a twelve-membered dilactonic pyrrolizidine alkaloid of retronecine type has been achieved through the enantioselective synthesis and regioselective coupling of (+)-retronecine (4) and (+)-integerrinecic acid (methylthio)methyl ether (6).