939019-35-9

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 114094-71-2 3-isopropoxy-4-phenylcyclobut-3-ene-1,2-dione 
• 160386-81-2 ((2S,5R,6S)-4-Bromo-5-methanesulfonyloxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 
• 160386-82-3 ((2S,5R,6S)-4-Bromo-5-methanesulfonyloxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid 
• 160386-80-1 ((2S,5R,6S)-4-Bromo-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 
• 160386-79-8 ((2S,6S)-4-Bromo-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 
• 160386-83-4 (3aS,5S,7aR)-7-Bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo<3,2-b>pyran-2-one 
• 160386-78-7 ((2S,6S)-6-Methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 
• 123976-40-9 ((2S,5R,6S)-5-Hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

A general enantiospecific synthesis of isochromanquinones is presented.This entails an efficient synthesis of (3aS,5S,7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furopyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose.Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c.In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized.In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.