951698-14-9Relevant articles and documents
Process Research and Development of an Enantiomerically Enriched Allyic Amine, One of the Key Intermediates for the Manufacture of Synthetic Tetracyclines
Zhang, Wu-Yan,Hogan, Philip C.,Chen, Chi-Li,Niu, John,Wang, Zhimin,Lafrance, Danny,Gilicky, Olga,Dunwoody, Nicholas,Ronn, Magnus
, p. 1784 - 1795 (2015/12/01)
A robust, cost-effective, and high yielding manufacturing process for enantiomerically enriched (S)-allylic amine 3, a key intermediate for fully synthetic tetracyclines have been developed. Two novel and scalable asymmetric vinylations resulting in high-to-excellent stereoselectivity have been developed for the key step. The final product is purified by an efficient crystallization of a l-tartaric salt. The process described has been used to manufacture ～350 kg of the tartaric salt of 3 with 99.0% ee in 8 steps (35% overall yield) from cheap and readily available dimethyl maleate.
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics
Brubaker, Jason D.,Myers, Andrew G.
, p. 3523 - 3525 (2008/02/11)
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics is reported. The route proceeds in nine steps (21% yield) from the commercial substance methyl 3-hydroxy-5-isoxazolecarboxylate. Key steps in the route involve enantioselective addition of divinylzinc to 3-benzyloxy-5-isoxazolecarboxaldehyde and an endo-selective intramolecular furan Diels-Alder cycloaddition reaction. The route described has provided more than 40 g of chromatographically pure 1 with 93% ee.
