A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones
C Alemany, J Bach, J Garcia, M López, AB Rodrı́guez
Index: Alemany, Carme; Bach, Jordi; Garcia, Jordi; Lopez, Marta; Rodriguez, Ana B. Tetrahedron, 2000 , vol. 56, # 47 p. 9305 - 9312
Full Text: HTML
Citation Number: 18
Abstract
The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3- ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C (3) stereocenter. This strategy has been applied to the synthesis of (3S, 4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc- ...
Related Articles:
[Yoo, Dongwon; Song, Jeeyun; Kang, Moon Sung; Kang, Eun-Sil; Kim, Young Gyu Tetrahedron Asymmetry, 2011 , vol. 22, # 16-17 p. 1700 - 1704]
[Sakaitani, Masahiro; Ohfune, Yasufumi Tetrahedron Letters, 1987 , vol. 28, # 34 p. 3987 - 3990]
[Camplo; Niddam; Barthelemy; Faury; Mourier; Simon; Charvet; Trabaud; Graciet; Chermann; Kraus European Journal of Medicinal Chemistry, 1995 , vol. 30, # 10 p. 789 - 800]
[European Journal of Medicinal Chemistry, , vol. 30, # 10 p. 789 - 800]
[European Journal of Medicinal Chemistry, , vol. 30, # 10 p. 789 - 800]