Crossley, Maxwell J.; Stamford, Andrew W. published an article in 1993, the title of the article was Concise, stereocontrolled synthesis of the C4 epimers of anticapsin and bacilysin: revision of the configurations of the natural products.Formula: C18H17NO4 And the article contains the following content:
The structures of anticapsin and bacilysin were shown to be I (R = H, H-Ala) rather than the reported C4 epimers II (R = H, H-L-Ala, R1 = H) via concise, stereocontrolled syntheses of II. Thus, Diels-Alder reaction of dehydroalanine ZNHC(CO2CH2Ph):CH2 (Z = PhCH2O2C) with 1-trimethylsilyloxy-1,3-cyclohexadiene regiospecifically gave a mixture of bicyclooctene stereoisomers, which were epoxidized to give endo epoxides III. Desilylation of III and alkoxide-induced ring cleavage gave racemic II (R = Z, R1 = CH2Ph) and its C2 epimer, which were separated by fractional crystallization Coupling of racemic II (R = H, R1 = Me) with Z-L-Ala-OH, separation of diastereomeric dipeptides, and deprotection gave (+)-II (R = H-Ala, R1 = H). The experimental process involved the reaction of Benzyl 2-(((benzyloxy)carbonyl)amino)acrylate(cas: 59524-07-1).Formula: C18H17NO4
The Article related to mol structure anticapsin bacilysin, asym synthesis anticapsin bacilysin diastereomer, Amino Acids, Peptides, and Proteins: Poly(Amino Acids) and Peptides and other aspects.Formula: C18H17NO4
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