@article { ISI:000232045500026, title = {Efficient synthesis of 2,3-aziridino-gamma-lactones from azetidin-2-ones}, journal = {Synlett}, number = {15}, year = {2005}, month = {SEP}, pages = {2370-2372}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

An efficient synthesis of enantiopure 2,3-aziridino-gamma-lactones from azetidin-2-ones is described. Acid-catalyzed tandem intramolecular azetidinone ring opening followed by aziridine ring formation via elimination of a mesylate group is the key step in this synthesis. 2,3-Aziridino-gamma-lactones are important precursors for biologically important glutamic acid derivatives.

}, keywords = {azetidin-2-ones, aziridines, glutamic acid, lactones}, issn = {0936-5214}, doi = {10.1055/s-2005-875563}, author = {Kale, Ajaykumar S. and Deshmukh, A. R. A. S.} } @article { ISI:000249453100008, title = {4-Formylazetidin-2-one as a useful building block for the formal synthesis of xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine}, journal = {Synthesis-Stuttgart }, volume = {17}, number = {17}, year = {2007}, month = {SEP}, pages = {2631-2636}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Stereoselective formal synthesis of xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine is described starting from an enantiopure formyl-substituted P-lactam. Grignard reaction of the N-Boc-protected-beta-lactam carbonyl group, followed by further transformations, provides a common intermediate for xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine.

}, keywords = {azetidin-2-one, beta-lactam, Grignard reaction, Phytosphingosine, Sphingosine}, issn = {0039-7881}, doi = {10.1055/s-2007-983815}, author = {Kale, Ajaykumar S. and Sakle, Prathmesh S. and Gumaste, Vikas K. and Deshmukh, Abdul Rakeeb A. S.} } @article { ISI:000246298900004, title = {Practical formal synthesis of D-(+)-biotin from 4-formylazetidin-2-one}, journal = {Synthesis-Stuttgart}, number = {8}, year = {2007}, month = {APR}, pages = {1159-1164}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

A practical synthesis of (3S,6R)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione, an important intermediate in the synthesis of biotin, from 4-formyl-3-mesyloxyazetidin-2-one has been achieved. Acid-catalyzed azetidin-2-one ring opening followed by a one-pot conversion of diamine hydrochloride to a cyclic urea and hydroxymethylene to chloromethylene by triphosgene to obtain (4S,5R)-methyl-1,3-dibenzyl-5-chloromethyl-2-oxoimidazolidine-4-carboxyl ate is the key step in this synthesis.

}, keywords = {azetidin-2-one, beta-Lactams, cyclization, Lactone, reduction}, issn = {0039-7881}, doi = {10.1055/s-2007-965992}, author = {Kale, Ajaykumar S. and Puranik, Vedavati G. and Deshmukh, Abdul Rakeeb A. S.} } @article { ISI:000264538000029, title = {Efficient formal synthesis of (S)-dapoxetine from enantiopure 3-hydroxy azetidin-2-one}, journal = {Tetrahedron}, volume = {65}, number = {12}, year = {2009}, month = {MAR}, pages = {2605-2609}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient formal synthesis of S-(+) dapoxetine starting from 3-hydroxy azetidin-2-one is described. The intermediate (S)-3-(dimethyl amino)-3-phenylpropan-1-ol was synthesized in enantiopure form starting with 3-hydroxy azetidin-2-one in seven steps. (c) 2008 Elsevier Ltd. All rights reserved.

}, keywords = {Azetidin 2 ones, beta-Lactams, Enantioselective synthesis, reduction, Staudinger reaction}, issn = {0040-4020}, doi = {10.1016/j.tet.2008.11.042}, author = {Chincholkar, Pinak M. and Kale, Ajaykumar S. and Gumaste, Vikas K. and Deshmukh, Abdul Rakeeb A. S.} }