158111-33-2

Upstream product

• 69610-41-9 Boc-L-Pro-H 
• 133120-82-8 (S)-2-(Propionyloxy)-1,1,2-triphenylethanol 
• 147-85-3 L-proline 
• 100-58-3 phenylmagnesium bromide 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 108998-83-0 (S)-1,1,2-triphenyl-1,2-ethanediol 
• 21210-43-5 (S)-Methyl mandelate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 

Downstream Products

• 158111-35-4 <2S-<2R*<(R*),α(R*),β(R*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester 

Relevant academic research and scientific papers

The Dolastatins. 17. Synthesis of Dolaproine and Related Diastereoisomers

A special challenge in accomplishing the total synthesis of dolastatin 10 (1) entailed deducing the absolute configuration of the new β-methoxy-γ-amino acid component dolaproine (2) as 2S,2'R,3'R and devising a stereoselective synthesis.Synthesis of this unusual (S)-proline-derived unit as its N-tert-butoxycarbonyl derivative (9b) and three stereoisomers (9a, 9c, 9d) has been summarized.The diastereoisomers were assembled by an aldol condensation between aldehyde 5, derived from (S)-proline, with chiral propionate 6, followed by methylation and cleavage of the chiral directing ester group by hydrogenolysis to afford methyl ethers 9a-d.The absolute stereochemistry of the diastereoisomers was determined by a combination of X-ray crystallographic analyses (of 9a and lactam 11b formed from isomer 7a) and high-field (400 MHz) NMR studies.By using each of these isomers in a series of dolastatin 10 syntheses the stereochemistry of the dolaproine (2) unit of natural (-)-dolastatin 10 (1) was shown to be 2S,2'R,3'R.