A Novel Synthesis of a Key Intermediate for (+)-Biotin from L-Aspartic Acid
- 1 January 2002
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2002 (03) , 361-364
- https://doi.org/10.1055/s-2002-20035
Abstract
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).Keywords
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