267889-01-0

Upstream product

• 267888-96-0 (2R,3R)-2-{(S)-1-[[2-(4-Benzyloxy-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-amino]-butyl}-3-hydroxy-succinic acid 4-ethyl ester 1-methyl ester 
• 267888-98-2 4-(tert-butyl-dimethyl-silanyloxy)-1-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-ethyl}-2-propyl-5-thioxo-pyrrolidine-3-carboxylic acid methyl ester 
• 267888-95-9 (S)-3-[[2-(4-Benzyloxy-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-amino]-hexanoic acid methyl ester 
• 267888-97-1 (2S,3R,4R)-4-Hydroxy-1-[2-(4-hydroxy-phenyl)-ethyl]-5-oxo-2-propyl-pyrrolidine-3-carboxylic acid methyl ester 
• 267888-94-8 [2-(4-Benzyloxy-phenyl)-ethyl]-((S)-1-phenyl-ethyl)-amine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 56441-69-1 2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester 
• 17138-28-2 (4-hydroxy-phenyl)-acetic acid ethyl ester 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 

Downstream Products

• 155944-28-8 (2S,3S,4R)-plakoridine A 

Relevant academic research and scientific papers

Total synthesis of (2S,3s,4R)-plakoridine A

The β-amino ester 6 is synthesized via the diastereoselective Michael addition of the lithium amide derived from amine 5 to methyl (E)-2-hexenoate. This ester is converted to the pyrrolidinone 8 via an aldol condensation/deprotection/cyclization. Transformation of the lactam 8 into thiolactam 11 followed by Eschenmoser sulfide contraction provides (2S,3S,4R)-plakoridine A. (C) 2000 Elsevier Science Ltd.