351458-87-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 131294-12-7 ethyl [(3R)-(tert-butyldimethylsilyloxy)-3-phenyl]propionate 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 500-99-2 3,5-dimethoxyphenol 
• 271600-97-6 3,5-dimethoxyphenyl-1-methoxymethyl ether 
• 351458-82-7 (R)-3-(tert-butyldimethylsylil)oxy-N-methoxy-N-methyl-benzenepropanamide 

Downstream Products

• 480-37-5 pinostrobin 
• 1036-72-2 Pinocembrin dimethyl ether 
• 862254-91-9 (R)-3-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropan-1-one 

Relevant academic research and scientific papers

Inter- and intramolecular Mitsunobu reaction based approaches to 2-substituted chromans and chroman-4-ones

Two approaches to optically active 2-substituted chromans and chroman-4-ones are described. The first utilized an intermolecular Mitsunobu reaction of a homochiral halopropanol and 2-bromophenol followed by cyclization to the 2-substituted chroman. In addition, a double lithiation procedure was developed to introduce additional functionality to the chroman. The second approach utilized an intramolecular Mitsunobu cyclization to give the 2-substituted chroman-4-one nucleus. The methodologies were applied to the syntheses of several biologically active natural and synthetic products.

Approaches to 2-substituted chroman-4-ones: Synthesis of (-)-pinostrobin

Two approaches to optically active 2-substituted chroman-4-ones are described. The first utilized the oxidation of a preformed chroman ring and the second an intramolecular Mitsunobu cyclization. The methodology was applied to the synthesis of the biologically active natural product (-)-pinostrobin (18).