A concise synthesis of (2S, 3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors
M Ikunaka, J Matsumoto, Y Nishimoto
Index: Ikunaka, Masaya; Matsumoto, Jun; Nishimoto, Yukifumi Tetrahedron Asymmetry, 2002 , vol. 13, # 11 p. 1201 - 1208
Full Text: HTML
Citation Number: 25
Abstract
Scalable syntheses of (2S, 3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5, 5-dimethyl-1, 3-thiazolidine-4- carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S, 3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N, N- ...
Related Articles:
Design and synthesis of highly potent HIV protease inhibitors with activity against resistant virus
[Lu, Zhijian; Raghavan, Subharekha; Bohn, Joann; Charest, Mark; Stahlhut, Mark W.; Rutkowski, Carrie A.; Simcoe, Amy L.; Olsen, David B.; Schleif, William A.; Carella, Anthony; Gabryelski, Lori; Jin, Lixia; Lin, Jiunn H.; Emini, Emilio; Chapman, Kevin; Tata, James R. Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 10 p. 1821 - 1824]
[Journal of Medicinal Chemistry, , vol. 42, # 10 p. 1789 - 1802]
[Tetrahedron Asymmetry, , vol. 13, # 11 p. 1201 - 1208]
[Tetrahedron Asymmetry, , vol. 13, # 11 p. 1201 - 1208]