@article { ISI:000266693600010, title = {Formal synthesis of (-) anisomycin via organocatalysis}, journal = {Arkivoc}, year = {2009}, month = {JAN}, pages = {88-94}, publisher = {ARKAT USA INC}, address = {C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}, abstract = {

An efficient formal synthesis of (-) anisomycin (1), a potent antibiotic agent, has been achieved in good yields and excellent diastereoselectivity. The key steps are proline-catalyzed sequential alpha-amination or alpha-aminoxylation of aldehyde 2 followed by tandem Horner-Wadsworth-Emmons olefination.

}, keywords = {alpha-Amination, alpha-aminoxylation, anisomycin, olefination, Proline}, issn = {1424-6376}, author = {Chouthaiwale, Pandurang V. and Kotkar, Shriram P. and Sudalai, Arumugam} } @article { ISI:000285370100022, title = {Facile enantioselective synthesis of (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol via proline-catalyzed asymmetric alpha-aminooxylation and alpha-amination of aldehyde}, journal = {Tetrahedron Letters}, volume = {51}, number = {50}, year = {2010}, month = {DEC}, pages = {6565-6567}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A high-yielding enantioselective synthesis of the bioactive (S)-N-(5-chlorothiophene-2-sulfonyl)beta,beta-diethylalaninol (1), a Notch-1-sparing gamma-secretase inhibitor metabolite (with EC50 = 28 nM) effective in reduction of All production in vivo, has been realized starting from readily available 3-pentanone. The key steps of the synthesis are proline-catalyzed alpha-aminooxylation and alpha-amination of aldehyde: the latter contributing an overall yield of 45.2\% and 98\% ee. (C) 2010 Elsevier Ltd. All rights reserved.

}, keywords = {alpha-Amination, alpha-Aminooxylation, Alzheimer{\textquoteright}s disease, Amino alcohol, Proline}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2010.10.029}, author = {Rawat, Varun and Chouthaiwale, Pandurang V. and Chavan, Vilas B. and Suryavanshi, Gurunath and Sudalai, Arumugam} } @article { ISI:000355354100003, title = {First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed alpha-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement}, journal = {Tetrahedron-Asymmetry}, volume = {26}, number = {10-11}, year = {2015}, month = {MAY}, pages = {548-552}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9\% and 98\% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are D-proline catalyzed sequential alpha-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate. (C) 2015 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2015.03.011}, author = {Ahuja, Brij Bhushan and Sudalai, Arumugam} } @article { ISI:000364968800017, title = {First enantioselective synthesis of surinamensinol B and a non-natural polysphorin analogue by a two-stereocentered hydrolytic kinetic resolution}, journal = {European Journal of Organic Chemistry}, volume = {33}, number = {33}, year = {2015}, month = {NOV}, pages = {7344-7351}, publisher = {WILEY-V C H VERLAG GMBH}, address = {POSTFACH 101161, 69451 WEINHEIM, GERMANY}, abstract = {

An efficient and economical approach to the synthesis of antitumor and anti-inflammatory surinamensinol B (1) and antimalarial polysphorin analogue 2 has been achieved with high enantiomeric purity (96\% ee) by starting from commercially available 3,4,5-trimethoxybenzaldehyde. The key steps of the strategy include a Co-catalyzed two-stereocentered hydrolytic kinetic resolution (HKR) of racemic 2[( methoxymethoxy)(3,4,5-trimethoxyphenyl)methyl] oxirane (13) as the chiral inducing step followed by a Mitsunobu reaction. Chiral epoxide 14 and chiral diol 15 were utilized in the syntheses of both compounds.

}, keywords = {Biological activity, Enantioselectivity, Kinetic resolution, Natural products, Total synthesis}, issn = {1434-193X}, doi = {10.1002/ejoc.201501009}, author = {Lalwani, Komal G. and Sudalai, Arumugam} } @article { ISI:000379437100016, title = {Formal enantioselective synthesis of (-)-epiquinamide by proline-catalyzed one-pot sequential -amination/propargylation of aldehyde and asymmetric dihydroxylation of olefin}, journal = {Synlett}, volume = {27}, number = {11}, year = {2016}, month = {JUL}, pages = {1699-1702}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Two independent routes to the formal synthesis of (-)-epiquinamide, have been described: the first route utilizes an l-proline-catalyzed one-pot sequential -amination/propargylation of aldehyde, while the second one employs asymmetric dihydroxylation as the key reaction to install the stereochemistry. While the first synthesis was accomplished in nine steps with 24.4\% overall yield and dr 9:1, the second strategy resulted in the synthesis in eight steps with 36.4\% overall yield and with perfect enantiocontrol.

}, keywords = {Amination, diastereoselective, Dihydroxylation, Proline, quinolizidine}, issn = {0936-5214}, doi = {10.1055/s-0035-1561956}, author = {Ahuja, Brij Bhushan and Emmanuvel, Lourdusamy and Sudalai, Arumugam} } @article { ISI:000368207600006, title = {Formal total synthesis of anti-helicobacter pylori agent (+)-spirolaxine methyl ether}, journal = {Tetrahedron Letters}, volume = {57}, number = {1}, year = {2016}, month = {JAN}, pages = {25-28}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A convergent, formal enantioselective synthesis of anti-Helicobacter pylori agent, (+)-spirolaxine methyl ether 2 has been achieved in high enantiomeric purity starting from commercially available 1,5-pentanediol. The strategy mainly comprises of the Noyori{\textquoteright}s asymmetric reduction and Brown allylation/Cu-catalyzed lactonization as the key step for the construction of key chiral intermediates, spiroketal 3 and phthalide fragment 4. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {Brown allylation, Cu-catalyzed lactonization, Noyori{\textquoteright}s asymmetric reduction, Phthalide, Spiroketal}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2015.11.047}, author = {Gadakh, Sunita K. and Sudalai, Arumugam} }