A novel synthesis of a key intermediate for (+)-biotin from L-aspartic acid

作者：Seki M^*; Shimizu T; Inubushi K

来源：Synthesis, 2002, (3): 361-364.

• vitamins
• stereoselective synthesis
• amino acids
• aldol reaction
• rearrangement

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 beta-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).

• 出版日期2002-2