@article { ISI:000228951700012, title = {Facile regioselective decomposition of tosylhydrazones: an application towards the synthesis of alpha-lipoic acid}, journal = {Synlett}, number = {7}, year = {2005}, month = {MAY}, pages = {1129-1132}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

A facile regioselective decomposition of tosylhydrazones using NaOH as a base in refluxing isopropyl alcohol is described. This finding has been Successfully applied towards the synthesis of (\±)-α-lipoic acid (1).

}, keywords = {alpha-lipoic acid, Olefins, Regioselectivity, tosylhydrazones}, issn = {0936-5214}, doi = {10.1055/s-2005-865217}, author = {Chavan, Subhash P. and Kale, R. R. and Pasupathy, K.} } @article { ISI:000228147400027, title = {First enantiospecific synthesis of (+)-beta-herbertenol}, journal = {Tetrahedron}, volume = {61}, number = {15}, year = {2005}, month = {APR}, pages = {3873-3879}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The first enantiospecific synthesis of (+)-beta-herbertenol, from naturally occurring R-(+)-citronellal, employing Taber{\textquoteright}s diazo decomposition protocol as the key step, is described. (c) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {citronellal, diazo decomposition, enantiospecific}, issn = {0040-4020}, doi = {10.1016/j.tet.2005.01.050}, author = {Chavan, Subhash P. and Thakkar, M. and Kharul, Rajendra K. and Pathak, A. B. and Bhosekar, Gaurav V. and Bhadbhade, Mohan M.} } @article { ISI:000241755300045, title = {First enantiospecific synthesis of (-)-parvifoline and (-)-curcuquinone}, journal = {Journal of Organic Chemistry}, volume = {71}, number = {23}, year = {2006}, month = {NOV}, pages = {8986-8988}, publisher = {AMER CHEMICAL SOC}, type = {Article}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

The first enantiospecific synthesis of (-)-parvifoline, employing ring-closing metathesis as the key step, and (-)-curcuquinone from naturally occurring (R)-(+)-citronellal is described.

}, issn = {0022-3263}, doi = {10.1021/jo061730d}, author = {Chavan, Subhash P. and Thakkar, Mahesh and Jogdand, Ganesh F. and Kalkote, Uttam R.} } @article { ISI:000243819800014, title = {Facile total synthesis of (+/-)-alpha-cuparenone employing diallylation and RCM as key steps}, journal = {Tetrahedron Letter}, volume = {48}, number = {6}, year = {2007}, month = {FEB}, pages = {965-966}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A short and concise total synthesis of alpha-cuparenone employing one-pot diallylation and RCM as the key steps is described. (c) 2006 Elsevier Ltd. All rights reserved.

}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.12.023}, author = {Chavan, Subhash P. and Dhawane, Abasaheb N. and Kalkote, Uttam R.} } @article { ISI:000243704000028, title = {First enantiospecific synthesis of (-)-heritol: absolute configuration determination}, journal = {Tetrahedron Letters}, volume = {48}, number = {4}, year = {2007}, month = {JAN}, pages = {643-646}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The first enantiospecific synthesis of (-)-heritol, from naturally occurring (R)-(+)-citronellal and confirmation of its absolute configuration, is described. (c) 2006 Elsevier Ltd. All rights reserved.

}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.11.123}, author = {Chavan, Subhash P. and Thakkar, Mahesh and Kalkote, Uttam R.} } @article { ISI:000272936000061, title = {Fluconazole analogues containing 2H-1,4-benzothiazin-3(4H)-one or 2H-1,4-benzoxazin-3(4H)-one moieties, a novel class of anti-Candida agents}, journal = {Bioorganic \& Medicinal Chemistry Letters}, volume = {20}, number = {2}, year = {2010}, month = {JAN}, pages = {722-725}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

As a part of our program to develop new antifungal agents, a series of fluconazole analogues was designed and synthesized wherein one of the triazole moieties in fluconazole was replaced with 2H-1,4-benzothiazin-3(4H)-one or 2H-1,4-benzoxazin-3(4H)-one moiety. The new chemical entities thus synthesized were screened against various fungi and it was observed that the compounds 4a and 4i are potent inhibitors of Candida strains. The structure-activity relationship for these compounds is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

}, keywords = {antifungal, Benzothiazinone, Benzoxazinone, Fluconazole}, issn = {0960-894X}, doi = {10.1016/j.bmcl.2009.11.071}, author = {Borate, Hanumant B. and Maujan, Suleman R. and Sawargave, Sangmeshwer P. and Chandavarkar, Mohan A. and Vaiude, Sharangi R. and Joshi, Vinay A. and Wakharkar, Radhika D. and Iyer, Ramki and Kelkar, Ramesh G. and Chavan, Subhash P. and Kunte, Sunita S.} } @article { ISI:000278451000017, title = {Formal synthesis of (+/-)-camptothecin via tricyclic lactone as key synthon}, journal = {Tetrahedron Letters}, volume = {51}, number = {23}, year = {2010}, month = {JUN}, pages = {3099-3101}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Formal synthesis of (+/-)-camptothecin via CDE tricyclic lactone employing tandem Michael addition, Dieckmann condensation and addition-elimination reaction as key steps starting from glycinate is described. (C) 2010 Elsevier Ltd. All rights reserved.

}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2010.04.019}, author = {Chavan, Subhash P. and Dhawane, Abasaheb N. and Kalkote, Uttam R.} } @article { ISI:000303429600017, title = {Formal synthesis of (-)-stemoamide using a useful epimerization at C-8}, journal = {Tetrahedron Letters}, volume = {53}, number = {21}, year = {2012}, month = {MAY}, pages = {2647-2650}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The formal synthesis of (-)-stemoamide was achieved starting from L-pyroglutamic acid. The key steps used are the allylation using BF3 center dot OEt2, ring closing metathesis, allylic oxidation and a novel epimerization at C8. (C) 2012 Elsevier Ltd. All rights reserved.

}, keywords = {Allylation, Allylic oxidation, Pyroglutamic acid, Ring closing metathesis, Stemoamide}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2012.03.054}, author = {Chavan, Subhash P. and Harale, Kishor R. and Puranik, Vedavati G. and Gawade, Rupesh L.} } @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: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 {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 {46992, title = {Furan-derived chiral bicycloaziridino lactone synthon: collective syntheses of oseltamivir phosphate (Tamiflu), (S)-pipecolic acid and its 3-hydroxy derivatives}, journal = {Chemistry-An Asian Journal}, volume = {15}, year = {2020}, month = {FEB }, pages = {415-424}, type = {Article}, abstract = {

A unified synthetic strategy for oseltamivir phosphate (tamiflu), (S)-pipecolic acid, and its 3-hydroxy derivatives from furan derived common chiral bicycloaziridino lactone synthon is described here. Key features are the short (4-steps), enantiopure, and decagram-scale synthesis of common chiral synthon from furan and its first-ever application in the total synthesis of biologically active compounds by taking the advantages of high functionalization ability of chiral synthon.

}, keywords = {Aziridine synthon, Chiral auxiliary, collective synthesis, Pipecolic acid, Tamiflu}, issn = {1861-4728}, doi = {10.1002/asia.201901523, Early Access Date = JAN 2020}, author = {Chavan, Subhash P. and Kadam, Appasaheb L. and Shinde, Shrikrishna S. and Gonnade, Rajesh G.} } @article {47664, title = {Formal synthesis of (-)-quinagolide: diastereoselective ring expansion via a bicyclic aziridinium ion strategy to access the octahydrobenzo[g]quinoline architecture}, journal = {Journal of Organic Chemistry}, volume = {86}, year = {2021}, month = {JUL }, pages = {9344-9352}, type = {Article}, abstract = {The diastereoselective formal synthesis of (-)-quinagolide, a D-2 receptor agonist, has been achieved. The synthesis started from L-pyroglutamic acid and relied on utilization of (a) a stereospecific catalytic hydrogenation and diastereoselective Horner-Emmons-Michael cascade to obtain functionalized prolinate, (b) a Lewis acid mediated Pummerer cyclization to construct a tricyclic fused ring system, and (c) a diastereoselective ring expansion via a bicyclic aziridinium intermediate to access the required 3-substituted piperidine scaffold.}, issn = {0022-3263}, doi = {10.1021/acs.joc.1c00603}, author = {Chavan, Subhash P. and Kawale, Sanket A. and Pisal, Mahesh M. and Kadam, Appasaheb L. and Gonnade, Rajesh G.} }