185300-95-2

Upstream product

• 185300-94-1 (R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one 
• 185300-90-7 (2R,3R)-3-Benzyloxy-2-methyl-butan-1-ol 
• 104486-82-0 (R)-3-((2S,3R)-3-Hydroxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 185300-92-9 (2S,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-1-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-6-methyl-octane-1,3-dione 
• 185300-83-8 (S)-3-[(2S,3R,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-3-hydroxy-6-methyl-octanoyl]-4-isopropyl-oxazolidin-2-one 
• 1054698-71-3 (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one 
• 185300-84-9 (3R,4S,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexanal 
• 185300-82-7 (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 128271-10-3 7-(3,4-dimethoxybenzyl)pederic acid 
• 185300-87-2 [(R)-1-((1S,2R)-2-Benzyloxy-1-methyl-propyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane 

Relevant academic research and scientific papers

Highly diastereoselective synthesis of pederic acid derivatives

A highly diastereoselective synthesis of methyl pederate (2) is described. A critical feature of the successful route is the introduction of the key C(7)-stereocenter at the stage of 4 via an enantioselective, syn-selective aldol reaction of aldehyde 5 and the chiral acyl oxazolidinone 6. Aldehyde 5, in turn, was prepared from the readily available aldol derivative 7 via a chelate-controlled reaction with allyltrimethylsilane. Intermediate 4 was elaborated to 2 via the intermediacy of 7-O-(3,4-dimethoxybenzyl)pederic acid (3), an intermediate in Kishi's syntheses of mycalamides A and B and onnamide A, by way of methyl pyranoside 16 and the fully protected pederic acid derivative 11.