Diastereoselective total synthesis of (+)-morusimic acid B, an amino acid from Morus alba-Science-Chemical Encyclopedia-lookchem

Diastereoselective total synthesis of (+)-morusimic acid B, an amino acid from Morus alba
Add time:08/18/2019 Source:sciencedirect.com

An efficient, flexible and diastereoselective synthesis of the naturally occurring pyrrolidine amino acid, (+)-morusimic acid B, has been accomplished. Starting from chiral, optically active (+)-(3S)-hydroxy butyric acid methyl ester the key steps of our synthesis are diastereoselective α-alkylation of its dianion to introduce the main part of the side chain, Curtius rearrangement of the hydrazide derivative to a 2-oxazolidinone followed by N→π-cyclization with mercury(II) acetate to generate the cis-2,5-disubstituted pyrrolidine ring. The remote C-3 stereocentre is established after chain elongation with the dianion of methyl acetoacetate and asymmetric hydrogenation of the resulting β-oxoester with Noyori's Ru(II)-(R)-BINAP catalyst.

We also recommend Trading Suppliers and Manufacturers of 4-Piperidin-1-yl-butyric acid ethyl ester (cas 116885-98-4). Pls Click Website Link as below: cas 116885-98-4 suppliers

Prev:Site mutations disrupt inter-helical H-bonds (α14W–α67T and β15W–β72S) involved in kinetic steps in the hemoglobin R→T transition without altering the free energies of oxygenation☆
Next: A new approach to cyclic hydroxamic acids: intramolecular cyclization of N-benzyloxy carbamates with carbon nucleophiles)

Click to view details

Encyclopedia