@article { ISI:000292472400016, title = {Protecting group directed stereoselective reduction of an epi-inosose: efficient synthesis of epi-inositol}, journal = {Tetrahedron Letters}, volume = {52}, number = {29}, year = {2011}, month = {JUL}, pages = {3756-3758}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A facile and high yielding synthesis of epi-inositol via stereoselective reduction of a pentaprotected epi-inosose is reported. Extent of stereoselectivity during the hydride reduction appears to depend on the ability of the substrate to complex with metal ions in the reducing agent. (C) 2011 Elsevier Ltd. All rights reserved.

}, keywords = {Cyclitol, Inositol, Polyol, reduction, Stereoselective}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2011.05.051}, author = {Patil, Madhuri T. and Krishnaswamy, Shobhana and Sarmah, Manash P. and Shashidhar, Mysore S.} } @article { ISI:000319647600012, title = {Orientation of the beta-hydroxyl group controls the diastereoselectivity during the hydride reduction and grignard reaction of inososes}, journal = {Tetrahedron}, volume = {69}, number = {25}, year = {2013}, month = {JUN}, pages = {5144-5151}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the beta-hydroxyl group (or its derivative). Presence of an axial beta-hydroxyl group generally results in the formation of relatively larger amount of the axial alcohol as a result of the reduction of the carbonyl group. The possible reasons for the observed differences in diastereoselectivity between the reactions of these isomeric epi- and scyllo-inososes have been discussed. The sequence of reactions reported here provides convenient access to C-allcylated inositols, such as iso-laminitol and iso-mytilitol as well as 2-O-methyl epi-inositol, an epimer of the naturally occurring ononitol. (C) 2013 Elsevier Ltd. All rights reserved.

}, keywords = {Cyclitol, diastereoselectivity, Grignard, Inositol, Nucleophile, reduction}, issn = {0040-4020}, doi = {10.1016/j.tet.2013.04.081}, author = {Jagdhane, Rajendra C. and Patil, Madhuri T. and Krishnaswamy, Shobhana and Shashidhar, Mysore S.} } @article {49699, title = {Desymmetrization of myo-inositol}, journal = {Carbohydrate Research}, volume = {553}, year = {2025}, month = {JUL}, pages = {109505}, type = {Article}, abstract = {

Chemistry and biology of phosphoinositols have been intensely investigated areas of research over the last 4-5 decades due to their involvement in cellular signal transduction pathways. Efficient laboratory synthesis of enantiomeric derivatives of inositols was a central issue since they were required for the delineation of the myo-inositol cycle as well as for the total synthesis of polyol based natural products and their derivatives. This essentially meant the development of competent methods for the desymmetrization of myo-inositol leading to the preparation of enantiomeric O-substituted derivatives of myo-inositol. This was approached by: the classical resolution methods involving separable diastereomers, the chiral pool synthesis, enzyme catalysis, asymmetric catalysis and preferential crystallization of enantiomers in a racemic conglomerate. This review summarizes results obtained in author{\textquoteright}s laboratory, as well as those reported in the literature on attempts at desymmetrization of myo-inositol.

}, keywords = {Conglomerate, Crystallization, Cyclitol, Enantiomers, Inositol, Lipid}, issn = {0008-6215}, doi = {10.1016/j.carres.2025.109505}, author = {Patil, Nivedita T. and Patil, Madhuri T. and Gonnade, Rajesh G. and Shashidhar, Mysore S.} }