@article { ISI:000252029800038, title = {Short and efficient synthesis of rubrolide E}, journal = {Synthetic Communications}, volume = {37}, number = {22-24}, year = {2007}, month = {DEC}, pages = {4253-4263}, publisher = {TAYLOR \& FRANCIS INC}, type = {Article}, address = {325 CHESTNUT ST, SUITE 800, PHILADELPHIA, PA 19106 USA}, abstract = {

Short and efficient synthesis of rubrolide E from commercially available 4-methoxyacetophenone, employing ring-closing metathesis, Knoevenagel condensation, and Reformatsky reactions, are the key steps are described.

}, keywords = {antibiotics, antitumor, Epoxide, Natural products, Total synthesis}, issn = {0039-7911}, doi = {10.1080/00397910701575665}, author = {Chavan, Subhash P. and Pathak, Ashok B. and Pandey, Ankur and Kalkote, Uttam R.} } @article { ISI:000255827100025, title = {Concise synthesis of protected (2S,4R)-4-hydroxyornithine}, journal = {Tetrahedron Letters}, volume = {49}, number = {20}, year = {2008}, month = {MAY}, pages = {3297-3299}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A short synthesis of the nonproteinogenic amino acid, (2S,4R)-4-hydroxyornithine is described. Starting from racemic benzyl glycidol, the scaffold of the target compound was constructed in high enantio- and diastereoselectivity using Jacobsen{\textquoteright}s hydrolytic kinetic resolution (HKR) and regioselective opening of an epoxide as key steps. (c) 2008 Elsevier Ltd. All rights reserved.

}, keywords = {Epoxide, Grignard reaction, hydroxyornithine, Jacobsen{\textquoteright}s HKR, Natural product}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2008.03.076}, author = {Pandey, Satyendra Kumar and Pandey, Menaka and Kumar, Pradeep} } @article { ISI:000276909600011, title = {Synthesis of aculeatins A and B via iterative hydrolytic kinetic resolution}, journal = {Synthesis-Stuttgart}, number = {9}, year = {2010}, month = {MAY}, pages = {1479-1484}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

A simple and concise approach for the synthesis of aculeatins A and B starting from (+/-)-epichlorohydrin is described. The synthetic strategy features Jacobsen{\textquoteright}s hydrolytic kinetic resolution and a Linchpin coupling as key steps.

}, keywords = {aculeatins, Epoxide, Hydrolytic kinetic resolution, Linchpin coupling, spirocyclization}, issn = {0039-7881}, doi = {10.1055/s-0029-1218687}, author = {Harbindu, Anand and Kumar, Pradeep} } @article { ISI:000289330000005, title = {Synthesis of C1- and C8a-epimers of (+)-castanospermine from D-glucose derived gamma,delta-epoxyazide: intramolecular 5-endo epoxide opening approach}, journal = {Tetrahedron}, volume = {67}, number = {15}, year = {2011}, month = {APR}, pages = {2773-2778}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A concise synthesis of two diastereomers of (+)-castanospermine namely 1- and 8a-epi-castanospermine 1b and 1c, respectively, is reported from D-glucose. The methodology involves stereoselective cross metathesis of D-glucose derived alkene 2 with 4-bromo-1-butene followed by azide displacement and m-CPBA oxidation to afford diastereomeric gamma,delta-epoxyazides 5a/5b. The Staudinger reaction of epoxyazide 5a followed by reaction with benzylchloroformate (CbzCl) unexpectedly furnished 1,3-oxazinan-2-one derivative 7 whose stereochemistry was establish by single crystal X-ray. This helps to assign the stereochemistry in the epoxidation reaction. The reduction of 5a/5b was then carried out by transfer hydrogenation to provide gamma,delta-epoxyamine that concomitantly undergoes intramolecular 5-endo-tet cyclization to afford hydroxypyrrolidine ring skeleton with sugar framework-a precursor to castanospermine analogues 1b/1c. (C) 2011 Elsevier Ltd. All rights reserved.

}, keywords = {alkaloids, Cross metathesis, D-Glucose, Epoxide, Oxazinanone, Polyhydroxy indolizidines}, issn = {0040-4020}, doi = {10.1016/j.tet.2011.02.030}, author = {Kalamkar, Navnath B. and Puranik, Vedavati G. and Dhavale, Dilip D.} } @article { ISI:000336700700003, title = {New enantioselective synthesis of (S)-2-ethoxy-3-(4-hydroxyphenyl)Propanoic acid esters (EEHP and IEHP), useful pharmaceutical intermediates of PPAR agonists}, journal = {Tetrahedron Letters}, volume = {55}, number = {21}, year = {2014}, month = {MAY}, pages = {3223-3226}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A new enantioselective synthetic route to the title compounds has been developed in a simple and practical way with high enantiopurity using commercially available starting material. (C) 2014 Elsevier Ltd. All rights reserved.

}, keywords = {EEHP, Epoxide, IEHP, PPAR agonists}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2014.04.021}, author = {Mujahid, Mohammad and Kunte, S. S. and Muthukrishnan, Murugan} } @article { ISI:000362919100021, title = {Mild regiospecific alcoholysis and aminolysis of epoxides catalyzed by zirconium(IV) oxynitrate}, journal = {Tetrahedron Letters}, volume = {56}, number = {43}, year = {2015}, month = {OCT}, pages = {5916-5919}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A regiospecific method for the ring-opening reaction of epoxides by the primary, secondary, tertiary alcohols, and aryl, aliphatic amines has been developed using non-toxic metal nitrate salt as a catalyst. The best results were obtained using zirconium(IV) oxynitrate among the various screened metal nitrate salts. The reported protocol works efficiently for styrene epoxide and aliphatic as well. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {Alcoholysis, Aminolysis, Epoxide, Lewis acid, Zirconia}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2015.09.031}, author = {Shinde, Sandip S. and Said, Madhukar S. and Surwase, Trupti B. and Kumar, Pradeep} } @article {46312, title = {Efficient synthesis of optically active neolignans ligraminol D and E}, journal = {Synthesis-Stuttgart}, volume = {51}, year = {2019}, month = {NOV}, pages = {4291-4295}, type = {Article}, abstract = {

Efficient syntheses of optically active neolignans ligraminol D and E were achieved in four simple steps starting from easily available chiral benzyl glycidyl ethers. The products were obtained in good overall yields and high enantioselectivities. The protocol might also be useful in the synthesis of other ligraminols or related neolignans.

}, keywords = {benzyl glycidyl ether, Epoxide, lignan, ligraminol, Mitsunobu}, issn = {0039-7881}, doi = {10.1055/s-0037-1611919}, author = {Ghotekar, Ganesh S. and Mujahid, M. and Muthukrishnan, M.} } @article {48909, title = {Efficient synthesis of optically active herbicide (S)-metolachlor via reductive ring opening of 2-methoxymethylaziridine}, journal = {Arkivoc}, year = {2023}, month = {JUL}, type = {Article}, abstract = {

An efficient synthesis of a well known chiral herbicide, (S)-metolachlor has been described using 2methoxymethylaziridine ring formation and reductive ring opening as key steps using commercially available (R)-epichlorohydrin. The present protocol delivers the required enantiomer of metolachlor in overall yield of 50.8\% and high enantiopurity (\>99\%).

}, keywords = {Aziridine, Epoxide, Epoxide ring opening, herbicide synthesis, Metolachlor}, issn = {1551-7004}, doi = {10.24820/ark.5550190.p011.954}, author = {Nalla, Viswanadh and Mujahid, Mohammad and Sasikumar, Murugesan and Mujumdar, Prashant and Muthukrishnan, Murugan} }