@article { ISI:000233209400079, title = {Synthesis of eupomatilone-6 and assignment of its absolute configuration}, journal = {Journal of Organic Chemistry}, volume = {70}, number = {23}, year = {2005}, month = {NOV}, pages = {9658-9661}, publisher = {AMER CHEMICAL SOC}, type = {Article}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

[GRAPHICS] The Zn-mediated Barbier reaction of the biarylaldehyde 8 with crotyl bromide followed by hydroboration and oxidation provided the gamma-butyrolactones 4 and 5. The stereoselective installation of methyl group at C-3 by using LiHMDS and MeI completed the synthesis of racemic eupomatilone-6 (2) and its diastereomer 3. The spectroscopic data of 2 was in fall agreement with reported spectra of natural product, thus confirming the revised relative configuration of eupomatilone-6. Similarly, an optically active (3R,4R,5S)-isomer of eupomatilone-6 (23) was prepared in which the aldol reaction with thiazolidinethione as a chiral auxiliary was employed as a key step. On the basis of the spectroscopic data and optical rotation values of 23, the absolute configuration of eupomatilone-6 was proposed.

}, issn = {0022-3263}, doi = {10.1021/jo0516234}, author = {Gurjar, Mukund K. and Karumudi, Bhargava and Ramana, C. V.} } @article { ISI:000242524100005, title = {Stereoselective synthesis of the polyketide chain of nagahamide A}, journal = {Tetrahedron-Asymmetry}, volume = {17}, number = {18}, year = {2006}, month = {OCT}, pages = {2609-2616}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A carbohydrate based approach for the enantioselective synthesis of the polyketide acid unit present in nagahamide A has been reported. Reductive ring opening of a chiral cyclopropane ketone group to enantioselectively install the methyl and propyl groups, is a salient feature of this synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2006.09.025}, author = {Mohapatra, Debendra K. and Chaudhuri, Siddhartha Ray and Sahoo, Gokarneswar and Gurjar, Mukund K.} } @article { ISI:000239885000005, title = {Synthesis of the spiro fused beta-lactone-gamma-lactam segment of oxazolomycin}, journal = {Tetrahedron Letters}, volume = {47}, number = {34}, year = {2006}, month = {AUG}, pages = {6031-6035}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An effective synthetic strategy for construction of the novel spiro-bicyclic beta-lactone-gamma-lactam system present in oxazolomycin has been demonstrated. The 3,4-disubstituted pyrrolidine ring system was constructed via an Evans aldol reaction. The spiro-beta-lactone ring was elaborated from a gem-hydroxymethyl moiety that was successfully installed by an aldol followed by a crossed Cannizzaro reaction. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {crossed Cannizzaro reaction, Evans{\textquoteright} aldol reaction, Garner{\textquoteright}s aldehyde, intramolecular Mitsunobu reaction, ruthenium tetroxide oxidation}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.06.117}, author = {Mohapatra, Debendra K. and Mondal, Dhananjoy and Gonnade, Rajesh G. and Chorghade, Mukund S. and Gurjar, Mukund K.} } @article { ISI:000238012800020, title = {Synthetic studies toward macrocidins: an RCM approach for the construction of the central cyclic core}, journal = {Tetrahedron Letters}, volume = {47}, number = {24}, year = {2006}, month = {JUN}, pages = {4061-4064}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The central macrocyclic core of the macrocidins was constructed using RCM as the key reaction. A preliminary investigation dealing with the key reactions, that is, the Dieckmann cyclization and the RCM, revealed that RCM of the beta-ketoamide is better than RCM of the corresponding acyltetramic acid. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {acyltetramic acid, Lacey-Dieckmann cyclization, macrocidins, Ring closing metathesis}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.03.192}, author = {Ramana, C. V. and Mondal, Mohabul A. and Puranik, Vedavati G. and Gurjar, Mukund K.} } @article { ISI:000250545100010, title = {Short and efficient synthetic strategy for the total syntheses of (S)-(+)- and (R)-(-)-Plakolide A}, journal = {European Journal of Organic Chemistry}, number = {30}, year = {2007}, month = {OCT}, pages = {5059-5063}, publisher = {WILEY-V C H VERLAG GMBH}, type = {Article}, address = {PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY}, abstract = {

Concise and efficient total syntheses of anticancer agents (S)(+)-Plakolide A and (R)-(-)-Plakolide A were accomplished in eight steps and an overall yield of 39 \% starting from geraniol. The key steps in our strategy are Sharpless asymmetric epoxidation, double elimination, and Stille coupling reactions.

}, keywords = {Cross-coupling, epoxidation, inhibitors, olefination}, issn = {1434-193X}, doi = {10.1002/ejoc.200700401}, author = {Mohapatra, Debendra K. and Pramanik, Chintnoy and Chorghade, Mukund S. and Gurjar, Mukund K.} } @article { ISI:000253154500023, title = {Syntheis of unusual tricyclic ring systems of biological interest}, journal = {Heterocycles}, volume = {73}, number = {1}, year = {2007}, month = {DEC}, pages = {269+}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

We describe a new synthesis of tricyclic scaffolds that incorporate a fusion of triazole with 1,4-benzodiazepine utilizing intramolecular {\textquoteleft}{\textquoteleft}click{\textquoteright}{\textquoteright} chemistry.

}, keywords = {1, 2, 3-Triazole, 4-benzodiazepine, Click chemistry, nitrogen rich polycyclic hetero-system, privileged structure}, issn = {0385-5414}, author = {Mohapatra, Debendra K. and Maity, Pradip K. and Chorghade, Mukund S. and Gurjar, Mukund K.} } @article { ISI:000245634500005, title = {Synthesis and evaluation of 4/5-hydroxy-2,3-diaryl(substituted)-cyclopent-2-en-1-ones as cis-restricted analogues of combretastatin A-4 as novel anticancer agents}, journal = {Journal of Medicinal Chemistry}, volume = {50}, number = {8}, year = {2007}, month = {APR}, pages = {1744-1753}, publisher = {AMER CHEMICAL SOC}, type = {Article}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

A new series of 2,3-diaryl-4/5-hydroxy-cyclopent-2-en-1-one analogues replacing the cis double bond of combretastatin A-4 (CA-4) by 4/5-hydroxy cyclopentenone moieties was designed and synthesized. The analogues displayed potent cytotoxic activity (IC50 \< 1 mu g/mL) against a panel of human cancer cell lines and endothelial cells. The most potent analogues 11 and 42 belonging to the 5-hydroxy cyclopentenone class were further evaluated for their mechanism of action. Both of the analogues led to cell cycle arrest at G2/M phase and induced apoptosis in endothelial cells. Antitubulin property of 42 was superior to 11 and comparable to CA-4. The compound 42 had better aqueous solubility, metabolic stability, and pharmacokinetic profile than CA-4 and also demonstrated significant tumor regression in the human colon xenograft model. Our data suggests that cis-restricted analogues of CA-4 are a new class of molecules that have the potential to be developed as novel agents for the treatment of cancer.

}, issn = {0022-2623}, doi = {10.1021/jm060938o}, author = {Gurjar, Mukund K. and Wakharkar, Radhika D. and Singh, Anu T. and Jaggi, Manu and Borate, Hanumant B. and Shinde, Popat D. and Verma, Ritu and Rajendran, Praveen and Dutt, Sarjana and Singh, Gurvinder and Sanna, Vinod K. and Singh, Manoj K. and Srivastava, Sanjay K. and Mahajan, Vishal A. and Jadhav, Vinod H. and Dutta, Kakali and Krishnan, Karthik and Chaudhary, Anika and Agarwal, Shiv K. and Mukherjee, Rama and Burman, Anand C.} } @article { ISI:000244678100004, title = {Synthesis of L-ido-configured six- and seven-membered carba-sugars}, journal = {Synthesis-Stuttgart}, number = {4}, year = {2007}, month = {FEB}, pages = {523-528}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Ring-closing olefin metathesis has been successfully applied to the modular construction of L-ido-configured six- and seven-membered carba-sugars.

}, keywords = {allylations, carbocycles, carbohydrates, Metathesis, Radical reactions}, issn = {0039-7881}, doi = {10.1055/s-2007-965899}, author = {Ramana, C. V. and Chaudhuri, Siddhartha Ray and Gurjar, Mukund K.} } @article { ISI:000245142600010, title = {Synthesis of the C19-C34 segment of amphidinolide C}, journal = {Synlett}, number = {4}, year = {2007}, month = {MAR}, pages = {567-570}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

The synthesis of the C19-C34 segment of amphidinolide C is described. The key steps include the Mioskowski{\textquoteright}s Lewis acid catalyzed epoxide opening with the alcohol, ring-closing metathesis, Wittig reaction, and Nozaki-Hiyama-Kishi coupling reaction.

}, keywords = {amphidinolide C, Cytotoxic, Nozaki-Hiyama-Kishi coupling, Ring-closing metathesis, Wittig reaction}, issn = {0936-5214}, doi = {10.1055/s-2007-967968}, author = {Mohapatra, Debendra K. and Rahaman, Hasibur and Chorghade, Mukund S. and Gurjar, Mukund K.} } @article { ISI:000264490200029, title = {Short total synthesis of (+)-cryptocarya diacetate}, journal = {Heterocycles}, volume = {77}, number = {2}, year = {2009}, month = {FEB}, pages = {945-952}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A short synthesis of (+)-cryptocarya diacetate was achieved by employing three component linchpin coupling, diastereoselective reduction of beta-hydroxyketone, and Z-selective HWE reaction as key transformations.

}, keywords = {Brook Rearrangement, cryptocarya diacetate, Diastereoselective Reduction, Horner-Wadswarth-Emmons Reaction, Linchpin coupling}, issn = {0385-5414}, doi = {10.3987/COM-08-S(F)107}, author = {Gurjar, Mukund K. and Raghupathi, Neelarapu and Chorghade, Mukund S.} } @article { ISI:000264490200027, title = {Studies toward the total synthesis of carba analogue of motif C OF M. TB cell wall AG complex}, journal = {Heterocycles}, volume = {77}, number = {2}, year = {2009}, month = {FEB}, pages = {909-925}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Herein we describe the synthesis of the carba analogue of motif C of arabinogalactan complex present in M tuberculosis cell wall. Pd(0) catalyzed allylic alkylation and Fraser-Reid{\textquoteright}s glycosidation are the two key reactions that were employed for the synthesis of central glycosyl accepter unit and the glycosylation respectively.

}, keywords = {Allylic Alkylation, desymmetrization, Fraser-Reid{\textquoteright}s Glycosidation, M. Tb Ag Complex, Mycobacterium tuberculosis}, issn = {0385-5414}, doi = {10.3987/COM-08-S(F)59}, author = {Gurjar, Mukund K. and Reddy, Challa Nageswar and Kalkote, Uttam R. and Chorghade, Mukund S.} } @article { ISI:000264490200023, title = {Syntheis of new chiral 5,6,7,8-tetrahydrotetrazolo[1,5-a]pyrazines from alpha-amino acid derivatives following {\textquoteleft}{\textquoteleft}click{\textquoteright}{\textquoteright} chemistry}, journal = {Heterocycles}, volume = {77}, number = {2}, year = {2009}, month = {FEB}, pages = {865-872}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient and practical synthesis of new chiral fused tetrazoles have been synthesized following [3+2] cycloaddition reaction starting from alpha-amino acid derivatives.

}, keywords = {Amino acid, Click chemistry, Hypertension, Nitrogen Rich System, Tetrazole}, issn = {0385-5414}, doi = {10.3987/COM-08-S(F)121}, author = {Mohapatra, Debendra K. and Maity, Pradip K. and Ghorpade, Ravindra V. and Gurjar, Mukund K.} } @article { ISI:000287635800023, title = {Stereoselective formal total synthesis of novel antibiotic (-)-centrolobine}, journal = {Heterocycles}, volume = {80}, number = {1}, year = {2010}, month = {JAN}, pages = {219-227}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A concise and stereoselective formal total synthesis of (-)-centrolobine is achieved utilizing Mioskowski{\textquoteright}s Lewis acid mediated epoxide opening followed by ring-closing metathesis as the key reaction.

}, keywords = {antibiotic, Centrolobine, Keck allylation, Ring-closing metathesis, Sharpless asymmetric epoxidation}, issn = {0385-5414}, doi = {10.3987/COM-08-S(S)1}, author = {Mohapatra, Debendra K. and Pal, Rita and Rahaman, Hasibur and Gurjar, Mukund K.} } @article { ISI:000287801700007, title = {Synthetic studies of superstolide A: a carbohydrate based synthesis of the C21-C26 segment}, journal = {Letters in Organic Chemistry}, volume = {7}, number = {8}, year = {2010}, month = {DEC}, pages = {657-660}, publisher = {BENTHAM SCIENCE PUBL LTD}, address = {EXECUTIVE STE Y26, PO BOX 7917, SAIF ZONE, 1200 BR SHARJAH, U ARAB EMIRATES}, abstract = {

The synthesis of C21-C26 fragment of superstolide A, starting from D-glucose diacetonide, involving regioselective ring opening of epoxide by Grignard reagent and regioselective stereospecefic hydroboration oxidation has been described.

}, keywords = {Chiral pool, Potent cytotoxic, Regioselective epoxide opening, Stereoselective hydroboration-oxidation, Superstolide A}, issn = {1570-1786}, doi = {10.2174/157017810793811704}, author = {Pal, Rita and Rahaman, Hasibur and Mohapatra, Debendra K. and Gurjar, Mukund K.} } @article {43435, title = {Synthesis of (+/-)-thia-calanolide A, its resolution and in vitro biological evaluation}, journal = {Arabian Journal of Chemistry}, volume = {9}, year = {2016}, month = {NOV}, pages = {S1597-S1602}, abstract = {A synthesis of (+/-)-thia-calanolide A 3 has been successfully accomplished starting from 3,5-dimethoxythiophenol 4, in six steps in an overall yield of 4.5\%. The key reaction involved Friedel-Crafts tigloylation of 5,7-dihydroxy-4-n-propyl thiocoumarin 6 employing an appropriate solvent of CS2-PhNO2 in a ratio of 7:3. In its biological evaluation for anti-HIV activity, (+/-)-thia-calanolide A 3 demonstrated comparatively less activity with calanolide A and its synthetic analogue aza-calanolide. Further, (+/-)-3 has been resolved by chiral HPLC to (+) and (-)-3. (C) 2012 Production and hosting by Elsevier B.V. on behalf of King Saud University.}, doi = {10.1016/j.arabjc.2012.04.027}, author = {Chopade, Anil U. and Chopade, Manojkumar U. and Chanda, Bhanu M. and Sawaikar, Dilip D. and Sonawane, Kiran B. and Gurjar, Mukund K.} }