429691-53-2Relevant academic research and scientific papers
A novel synthesis of a key intermediate for (+)-biotin from L-aspartic acid
Seki, Masahiko,Shimizu, Toshiaki,Inubushi, Koichi
, p. 361 - 364 (2007/10/03)
The aldol reaction of an N-Cbz-3-amino-4-butanolide 4, derived from L-aspartic acid, with formaldehyde gave the trans-disubstituted 3-amino-4-butanolide 5 stereoselectively. Following protection of the hydroxyl group of 5, amidation and oxidation provided the β-substituted L-asparagine derivative 6. The Hofmann rearrangement of 6 with sodium hypochlorite in the presence of sodium hydroxide and subsequent hydrogenation gave the bicyclic lactone 11, which upon dibenzylation and thionation, gave the thiolactone 2, a key intermediate for the synthesis of (+)-biotin (1).
