@article { ISI:000323093300010, title = {Short synthesis of (2S,3S)-3-hydroxypipecolic acid}, journal = {Tetrahedron Letters}, volume = {54}, number = {36}, year = {2013}, month = {SEP}, pages = {4851-4853}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A convenient synthesis of (2S,3S)-3-hydroxypipecolic acid starting from cheap and abundant L-(+)-tartaric acid has been achieved. The strategy employs selective ester reduction and reductive lactamization as key steps. (C) 2013 Elsevier Ltd. All rights reserved.

}, keywords = {Reductive lactamization, Selective deprotection, Wittig reaction}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2013.06.111}, author = {Chavan, Subhash P. and Harale, Kishor R. and Pawar, Kailash P.} } @article { ISI:000341083400001, title = {Novel, concise and efficient protocol for non-natural piperidine compounds}, journal = {RSC Advances}, volume = {4}, number = {62}, year = {2014}, month = {JUL}, pages = {32594-32598}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Formal synthesis of L-altro-1-deoxynojirimycin, cis-3-hydroxypipecolic acid along with synthesis of (R)-piperidinol and a conceptually different advanced intermediate for non-natural piperidine alkaloids is reported from cis-butene-1,4-diol. The key reactions involved are Johnson-Claisen rearrangement, Sharpless asymmetric dihydroxylation, reductive lactamization and novel regioselective elimination.

}, issn = {2046-2069}, doi = {10.1039/c4ra04558k}, author = {Chavan, Subhash P. and Dumare, Nilesh B. and Pawar, Kailash P.} } @article {46405, title = {Protecting group free and scalable approach towards total synthesis of (-)-venlafaxine}, journal = {RSC Advances}, volume = {4}, year = {2014}, month = {FEB}, pages = {14468-14470}, type = {Article}, abstract = {

A protecting group free asymmetric total synthesis of (-)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53\% overall yield in 6 steps for total synthesis of (-)-venlafaxine.

}, issn = {2046-2069}, doi = {10.1039/c4ra00840e}, author = {Chavan, Subhash P. and Pawar, Kailash P. and Garai, Sumanta} } @article { ISI:000341938100024, title = {Total syntheses of D-allo-1-deoxynojirimycin and L-talo-1-deoxynojirimycin via reductive cyclization}, journal = {RSC Advances}, volume = {4}, number = {77}, year = {2014}, month = {AUG}, pages = {40852-40858}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Synthesis of a polyhydroxypiperidine framework for L-talo-1-deoxynojirimycin and D-allo-1-deoxynojirimycin was achieved from L-tartaric acid by employing flash dihydroxylation and reductive lactamisation as the key steps.

}, issn = {2046-2069}, doi = {10.1039/c4ra06884j}, author = {Chavan, Subhash P. and Dumare, Nilesh B. and Pawar, Kailash P.} } @article {45947, title = {Chirality induction and chiron approaches to enantioselective total synthesis of alpha-lipoic acid}, journal = {Tetrahedron}, volume = {71}, year = {2015}, month = {JUN }, pages = {4213-4218}, type = {Article}, abstract = {

An efficient, short and convenient asymmetric synthesis of (R)-(+)-lipoic acid in seven steps from chiral hydroxy aldehyde with 32.5\% overall yield is described. Synthesis of S and R enantiomers of a-lipoic acid from cis-1,4-butene diol derived chiral lactone is reported with 34 \% overall yield. The present synthesis involves use of simple reaction conditions making it a convenient synthesis. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {Chiral pool, Chirality induction, enantioselective, Lipoic acid, sharpless asymmetric dihydroxylation}, issn = {0040-4020}, doi = {10.1016/j.tet.2015.04.090}, author = {Chavan, Subhash P. and Pawar, Kailash P. and Praveen, Ch and Patil, Niteen B.} } @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:000349061500011, title = {Formal syntheses of (2R,3R)-3-hydroxy pipecolic acid and (2R,3S)-3-hydroxy pipecolic acid from L-ascorbic acid}, journal = {Tetrahedron Letters}, volume = {56}, number = {6}, year = {2015}, month = {FEB}, pages = {805-807}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Formal syntheses of both cis and trans 3-hydroxy pipecolic acids is achieved from L-ascorbic acid. Present synthesis describes use of chiral pool approach in which epimerization, Staudinger reaction and Cyclization reactions were employed as key steps. (C) 2014 Elsevier Ltd. All rights reserved.

}, keywords = {3-Hydroxy pipecolic acid, cyclization, Epimerization, L-Ascorbic acid}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2014.12.103}, author = {Chavan, Subhash P. and Dumare, Nilesh B. and Pawar, Kailash P.} } @article { ISI:000351584500007, title = {Synthesis of 3-ethyl-4-metyl-1h,5-dihydro-2h-pyrrol-2-one by novel palladium(ii)-catalyzed cyclization and ring-closing metathesis}, journal = {Synthesis-Stuttgart}, volume = {47}, number = {7}, year = {2015}, month = {APR}, pages = {955-960}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one is described starting from commercially available allylamine and 4-methoxybenzylamine employing palladium-catalyzed cyclization or ring-closing metathesis as the key steps.

}, keywords = {antidiabetic, cyclization, glimepiride, lactams, metabolite, pyrrolinone, Ring-closing metathesis}, issn = {0039-7881}, doi = {10.1055/s-0034-1379985}, author = {Chavan, Subhash P. and Pathak, Ashok B. and Pawar, Kailash P.} } @article { ISI:000352671600006, title = {Total synthesis of (R)-lipoic acid and (S)-lipoic acid via an Mn (III)-salen-catalyzed oxidative kinetic resolution}, journal = {Tetrahedron-Asymmetry}, volume = {26}, number = {5-6}, year = {2015}, month = {MAR}, pages = {281-287}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The asymmetric synthesis of both the antipodes of alpha-lipoic acid is described. The total synthesis of racemic and asymmetric lipoic acid is achieved from propane 1,3-diol. This work reports the use of Mn (III)-salen-catalyzed oxidative kinetic resolution as the key step to obtain enantiomerically pure (R)- and (S)-lipoic acid. The undesired product formed during the resolution can be recycled to achieve the desired isomer. (C) 2015 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2015.02.001}, author = {Purude, Abhijeet N. and Pawar, Kailash P. and Patil, Niteen B. and Kalkote, Uttam R. and Chavan, Subhash P.} } @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.} }