A facile synthesis of a key intermediate for (+)-biotin via strecker reaction

作者：Mori Y; Kimura M; Seki M^*

来源：Synthesis (Germany), 2003, (15): 2311-2316.

DOI：10.1055/s-2003-42399

• amino acids
• amino aldehydes
• ring closure
• stereoselectivity
• vitamins
• biotin
• Strecker reaction

The Strecker reaction of (2R,4R)-2-phenyl-3-phenoxycarbonylthiazolidine-4-carbaldehyde (4b), which was readily prepared from L-cysteine, with benzylamine and trimethylsilyl cyanide provided alpha-amino nitrile 5b stereoselectively (syn-anti, 2: 1). Amidation of 5b and subsequent cyclization gave bicyclic compound 6, which, upon reduction with zinc dust, hydrolysis and subsequent cyclization, furnished thiolactone 2, a key intermediate for (+)-biotin (1).

• 出版日期2003-10-31