@article { ISI:000344825300009, title = {Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid}, journal = {Tetrahedron Letters}, volume = {55}, number = {47}, year = {2014}, month = {NOV}, pages = {6423-6426}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization and selective N-debenzylation over O-debenzylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.

}, keywords = {3-Hydroxypipecolic acid, Aziridine ring opening, Aziridine-2-carboxylate, Piperidine alkaloids, Selective debenzylation}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2014.09.118}, author = {Chavan, Subhash P. and Khairnar, Lalit B. and Chavan, Prakash N. and Dumare, Nilesh B. and Kalbhor, Dinesh B. and Gonnade, Rajesh G.} } @article { ISI:000343624300007, title = {Efficient and mild method for preparation of allylic amines from aziridine-2-alcohols using PPh3/I-2/imidazole}, journal = {Tetrahedron Letters}, volume = {55}, number = {43}, year = {2014}, month = {OCT}, pages = {5905-5907}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Allylic amines are synthesized in good to excellent yields by treatment of aziridine-2-alcohols with PPh3/I-2/imidazole in THF as solvent under mild conditions. (C) 2014 Elsevier Ltd. All rights reserved.

}, keywords = {Chiral allylic amine, Chiral aziridine-2-alcohols, PPh3/iodine/imidazole, Reductive elimination}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2014.08.078}, author = {Chavan, Subhash P. and Khairnar, Lalit B. and Chavan, Prakash N.} } @article { ISI:000345902500007, title = {Facile and convenient synthesis of (+/-)-Biotin via MgCl2/Et3N-mediated C-C coupling and mitsunobu reaction}, journal = {Synlett}, volume = {25}, number = {20}, year = {2014}, month = {DEC}, pages = {2879-2882}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

A synthesis of (+/-)-biotin is described starting from simple starting materials viz. cyclohexanone and amino malonic acid ester. The key steps involved are MgCl2/Et3N coupling of amino malonic acid ester derivative and acid chloride, Mitsunobu reaction, ozonolysis, Staudinger reduction, novel urea formation, and subsequent dibenzylation. This approach is economical and involves high-yielding steps and simple reaction conditions.

}, keywords = {Appel reaction, biotin, Mitsunobu reaction, Ozonolysis, Staudinger reduction}, issn = {0936-5214}, doi = {10.1055/s-0034-1379365}, author = {Chavan, Subhash P. and Chavan, Prakash N. and Lasonkar, Pradeep B. and Khairnar, Lalit B. and Kadam, Appasaheb L.} } @article { ISI:000342873800010, title = {Short enantioselective total synthesis of (R)- and (S)-pipecolic acid}, journal = {Tetrahedron-Asymmetry}, volume = {25}, number = {16-17}, year = {2014}, month = {SEP}, pages = {1246-1251}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A convenient and practical total synthesis of (R)- and (S)-pipecolic acid has been achieved by utilizing chiral cis-aziridine-2-carboxylate as the common synthetic precursor. The synthesis involves regioselective reductive cleavage of the aziridine ring and Wittig olefination as key reactions. (C) 2014 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2014.08.001}, author = {Chavan, Subhash P. and Khairnar, Lalit B. and Chavan, Prakash N. and Kalbhor, Dinesh B.} } @article { ISI:000345660300032, title = {Stereospecific synthetic approach towards tamiflu using the ramberg-backlund reaction from cysteine hydrochloride}, journal = {RSC Advances}, volume = {4}, number = {107}, year = {2014}, month = {NOV}, pages = {62281-62284}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

The stereospecific formal synthesis of Tamiflu from L-cysteine hydrochloride as the chiral source is described. The notable feature of the present strategy is the Ramberg-Backlund reaction and Sharpless-Reich protocol as the key chemical transformations to access the cyclohexene skeleton of Tamiflu.

}, issn = {2046-2069}, doi = {10.1039/c4ra10391b}, author = {Chavan, Subhash P. and Chavan, Prakash N. and Gonnade, Rajesh G.} } @article { ISI:000355987900093, title = {Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, beta-(+)-conhydrine and (-)-swainsonine using an aziridine derived common chiral synthon}, journal = {RSC Advances}, volume = {5}, number = {62}, year = {2015}, month = {MAY}, pages = {50580-50590}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Concise total syntheses of (R)-pipecolic acid, (R)-ethyl-6-oxopipecolate, (2R, 3R)-3-hydroxypipecolic acid and formal syntheses of beta-(+)-conhydrine, (-)-lentiginosine, (-)-swainsonine and 1,2-di-epi-swainsonine have been accomplished starting from a common chiral synthon. The present strategy employs regioselective aziridine ring opening, Wittig olefination and RCM as the key chemical transformations.

}, issn = {2046-2069}, doi = {10.1039/c5ra06429e}, author = {Chavan, Subhash P. and Khairnar, Lalit B. and Pawar, Kailash P. and Chavan, Prakash N. and Kawale, Sanket A.} } @article { ISI:000377612300010, title = {Asymmetric total synthesis of L-allo-1-deoxynojirimycin}, journal = {Arkivoc}, number = {2}, year = {2016}, month = {OCT}, pages = {137-147}, publisher = {ARKAT USA INC}, address = {C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}, abstract = {

Asymmetric total synthesis of L-allo-1-deoxynojirimycin (L-allo-DNJ) was achieved from cis-butene-1,4-diol by employing Sharpless asymmetric dihydroxylation, stereoselective flash dihydroxylation and ring enlargement reactions as key steps.

}, keywords = {diastereoselective flash dihydroxylation, ring-enlargement reaction, sharpless asymmetric dihydroxylation}, issn = {1551-7004}, doi = {10.3998/ark.5550190.p009.295}, author = {Chavan, Subhash P. and Dumare, Nilesh B. and Pawar, Kailash P. and Chavan, Prakash N. and Khairnar, Lalit B.} } @article {46436, title = {Formal synthesis of brivaracetam: a key to construct the pyrrolidone scaffold using Pd-catalyzed oxidative cyclization and ring-closing metathesis reaction}, journal = {Tetrahedron Letters}, volume = {60}, year = {2019}, month = {NOV}, pages = {151249}, type = {Article}, abstract = {

A short and efficient synthetic approach for brivaracetam has been accomplished via two different routes which utilize Pd-catalyzed oxidative cyclization and ring-closing metathesis (RCM) as the key reaction. These two routes are novel, simple, scalable and rely on (E)-pent-2-en-1-ol and valeraldehyde as a commercially available starting material to yield brivaracetam with good overall yield. (C) 2019 Published by Elsevier Ltd.

}, keywords = {Antiepileptic drugs, Pd-catalyzed oxidative cyclization, pyrrolinone, Ring-closing metathesis reaction}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2019.151249}, author = {Chavan, Subhash P. and Kawale, Sanket A. and Chavan, Prakash N.} } @article {46597, title = {Chiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid (vol 55, pg 6423, 2014)}, journal = {Tetrahedron Letters}, volume = {61}, year = {2020}, month = {DEC }, pages = {152644}, type = {Correction}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2020.152644}, author = {Chavan, Subhash P. and Khairnar, Lalit B. and Chavan, Prakash N. and Dumare, Nilesh B. and Kalbhor, Dinesh B. and Gonnade, Rajesh G.} }