@article { ISI:000242873400011, title = {General strategy for a short and efficient synthesis of 3-hydroxy-4-methylprolines (HMP)}, journal = {Tetrahedron Letters}, volume = {47}, number = {52}, year = {2006}, month = {DEC}, pages = {9215-9219}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The non-proteinogenic amino acid 3-hydroxy-4-methylproline (HMP) is an active constituent of some potent antimicrobials including echinocandins, nostopeptins, pneumocandins, sporiofungin and mulundocandins. A synthesis has been achieved in 10 steps with 29\% overall yield; the Evans{\textquoteright} aldol reaction using Crimmins{\textquoteright} modified method was pivotal to the success of the strategy. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {3, 4-disubstituted proline, Crimmins{\textquoteright} aldol reaction, Garner{\textquoteright}s aldehyde, non-proteinogenic amino acids, RUO4 mediated oxidation}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.10.137}, author = {Mohapatra, Debendra K. and Mondal, Dhananjoy and Chorghade, Mukund S. and Gurjar, Mukund K.} } @article { ISI:000239885000005, title = {Synthesis of the spiro fused beta-lactone-gamma-lactam segment of oxazolomycin}, journal = {Tetrahedron Letters}, volume = {47}, number = {34}, year = {2006}, month = {AUG}, pages = {6031-6035}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An effective synthetic strategy for construction of the novel spiro-bicyclic beta-lactone-gamma-lactam system present in oxazolomycin has been demonstrated. The 3,4-disubstituted pyrrolidine ring system was constructed via an Evans aldol reaction. The spiro-beta-lactone ring was elaborated from a gem-hydroxymethyl moiety that was successfully installed by an aldol followed by a crossed Cannizzaro reaction. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {crossed Cannizzaro reaction, Evans{\textquoteright} aldol reaction, Garner{\textquoteright}s aldehyde, intramolecular Mitsunobu reaction, ruthenium tetroxide oxidation}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.06.117}, author = {Mohapatra, Debendra K. and Mondal, Dhananjoy and Gonnade, Rajesh G. and Chorghade, Mukund S. and Gurjar, Mukund K.} } @article { ISI:000282106400002, title = {Concise synthesis of (2S,3S,4S)-2-(Hydroxymethyl)pyrrolidine-3,4-diol (LAB1)}, journal = {Synthesis-Stuttgart}, number = {18}, year = {2010}, month = {SEP}, pages = {3063-3066}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1) from Garner{\textquoteright}s aldehyde is described using the Sharpless asymmetric dihydroxylation as the key step.

}, keywords = {alkaloid, azasugars, diastereoselectivity, Garner{\textquoteright}s aldehyde, pyrrolidine, Wittig reaction}, issn = {0039-7881}, doi = {10.1055/s-0030-1258185}, author = {Upadhyay, Puspesh K. and Kumar, Pradeep} } @article { ISI:000282106600012, title = {Synthetic view of an analogue of the spiro-beta-lactone-gamma-lactam ring in oxazolomycins and lajollamycin}, journal = {Synthesis-Stuttgart}, number = {19}, year = {2010}, month = {OCT}, pages = {3301-3308}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Herein, we describe a new synthetic strategy towards an analogue of the spiro-beta-lactone-gamma-lactam ring found in a class of potent antibiotics, the oxazolomycins and lajollamycin. The synthetic idea relies on the construction of two rings (beta-lactone and pyrrolidinone). The formation of the spiro-beta-lactone was accomplished by a crossed Cannizzaro reaction, while the 3,4-disubstituted pyrrolidinone ring was constructed by a titanium(IV) chloride mediated chelation-controlled double stereodifferentiating Crimmins aldol reaction of Garner{\textquoteright}s aldehyde.

}, keywords = {Crimmins aldol reaction, crossed Cannizzaro reaction, Garner{\textquoteright}s aldehyde, lactones, Mitsunobu reaction, pyrrolidine}, issn = {0039-7881}, doi = {10.1055/s-0030-1257872}, author = {Mondal, Dhananjoy and Bera, Smritilekha} } @article { ISI:000324460900018, title = {Concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate}, journal = {Arkivoc}, number = {2}, year = {2013}, month = {OCT}, pages = {220-227}, publisher = {ARKAT USA INC}, address = {C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}, abstract = {

An efficient synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate 1, a common intermediate for various polyhydroxylated piperidines is reported in six steps with 32\% overall yield starting from Garner{\textquoteright}s aldehyde. The key steps include the diastereoselective nucleophilic addition and intramolecular cyclization. (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate is a common precursor for the synthesis of 1-deoxy-L-mannojirimycin, 1-deoxy-L-idonojirimycin, L-fagomycin and related analogues.

}, keywords = {cyclization, Garner{\textquoteright}s aldehyde, nucleophilic addition, polyhydroxy piperidines}, issn = {1551-7004}, author = {Ramalingam, S. and Bhise, Ankushkumar D. and Show, Krishanu and Kumar, Pradeep} }