161219-33-6Relevant articles and documents
Trichosporon cutaneum-promoted deracemization of (±)-2-hydroxindan-1-one: a mechanistic study
Cazetta, Tarcila,Lunardi, Ines,Conceicao, Gelson J.A.,Moran, Paulo J.S.,Rodrigues, J. Augusto R.
, p. 2030 - 2036 (2008/02/11)
A mechanistic study of the deracemization of (±)-2-hydroxy-1-indanone mediated by the yeast Trichosporon cutaneum to afford pure (1S,2R)-1,2-indandiol is reported. The key aspect of the study was the use of pure (R)- and (S)-2-hydroxy-1-indanone enantiomers to ensure reliable conclusions. Experiments in the absence of yeast cells or using dead cells disclosed that the pure enantiomers were not racemized, which suggest that the whole dynamic kinetic resolution process is enzymatic in character. When living yeast cells were used the (R)-substrate was smoothly converted to (1S,2R)-1,2-indandiol, whilst the (S)-2-hydroxy-1-indanone was converted to the same diol through a more complex fashion, which requires a more lengthy oxidation-reduction pathway having the 1,2-indanedione as an achiral intermediate. An unexpected observation was that 1,2-indanone acts as a moderate inhibitor of the reductive enzymes acting in the conversion of (R)-2-hydroxy-1-indanone to (1S,2R)-1,2-indandiol.
A practical synthesis of (1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor, indinavir
Kajiro, Hiroshi,Mitamura, Shuichi,Mori, Atsunori,Hiyama, Tamejiro
, p. 1093 - 1100 (2007/10/03)
A synthesis of (1S,2R)-1-amino-2-indanol (1), a key component of an HIV protease inhibitor, was accomplished through (R)-2-hydroxy-1-indanone ((R)- 3), which was prepared by an intramolecular Friedel-Crafts acylation of (R)2- acetoxy-3-phenylpropanoic acid readily available from D-(R)-phenylalanine. Alternatively, (R)-3 was obtained by an enzymatic resolution of (±)-2- acetoxy-1-indanone. Ketone (R)-3 was convened into 1 through an oxime formation and diastereoselective hydrogenation.
A practical synthesis of (1S, 2R)-1-amino-2-indanol, a key component of HIV protease inhibitor, indinavir
Kajiro, Hiroshi,Mitamura, Shu-Ichi,Mori, Atsunori,Hiyama, Tamejiro
, p. 51 - 52 (2007/10/03)
The synthesis of (1S,2R)-1-amino-2-indanol, a key component of HIV protease inhibitor, is accomplished in eight steps from D-phenylalanine. The starting material is converted into 2-acetoxy-1-indanone in four steps involving intramolecular Friedel-Crafts cyclization. The stereochemically labile α-acetoxy ketone is hydrolyzed to 2-hydroxy-1-indanone using a catalytic amount of scandium triflate without any loss of the optical purity. Diastereoselective hydrogenation of α-hydroxy oxime, derived from the α-hydroxy ketone, gives the amino alcohol in 96% cis-selectivity. Optical purity of the starting material is perfectly retained throughout the transformations.
