A convergent synthesis of all S-configurated diastereoisomer of RP-66453 (aS,S,S,S,S,S), a peptide secondary metabolite, has been developed. The synthesis is notable for its brevity, partly because functionalized amino acids can be used directly. By combination of chem. evidence and NMR data, the abs. configuration of RP-66453 was detd. to be (aR,S,S,S,S,S). It is interesting to note that nature created RP-66453 with a thermodynamically less stable atropisomer, while lab. synthesis using intramol. Suzuki-Miyarura coupling as the last ring-closure step produced the thermodynamically more stable isomer. [on SciFinder (R)]
Title
Total synthesis of an atropdiastereomer of RP-66453 and determination of its absolute configuration
Published in
Angewandte Chemie, International Edition
Volume
42
Issue
35
Pages
4238-4241
Date
2003
ISSN
1433-7851
Note
CAN 139:396155
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
625096-20-0P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (total synthesis of atropdiastereomer of peptide secondary metabolite RP-66453 and detn. of its abs. configuration); 1421-65-4; 13139-16-7; 73183-34-3; 113850-71-8; 174698-43-2 (RP-66453); 178744-39-3 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of atropdiastereomer of peptide secondary metabolite RP-66453 and detn. of its abs. configuration); 612484-56-7P; 623941-89-9P; 623941-90-2P; 625096-21-1P; 625096-22-2P; 625096-23-3P; 625096-25-5P; 625096-26-6P; 625096-27-7P; 625096-28-8P; 625096-29-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of atropdiastereomer of peptide secondary metabolite RP-66453 and detn. of its abs. configuration); 625096-24-4P; 675832-36-7P Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of atropdiastereomer of peptide secondary metabolite RP-66453 and detn. of its abs. configuration)
Record creation date
2010-11-25
