@article { ISI:000316693100020, title = {Synthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans-cis isomerisation of the enamide macrocycle}, journal = {Chemical Communications}, volume = {49}, number = {32}, year = {2013}, month = {MAR}, pages = {3342-3344}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Concise and protecting-group free synthesis of ent-palmyrolide A and (-)-cis-palmyrolide A were achieved starting from commercially available (S)-citronellal. The key fragment of palmyrolide A, {\textquoteleft}{\textquoteleft}(5S,7S)-7-hydroxy-5,8,8-trimethylnonanamide{\textquoteright}{\textquoteright}, which makes up the most challenging part of the target molecule, was prepared in just three steps. A plausible mechanism for the trans-cis isomerization of the double bond in the macrocycle has been investigated.

}, issn = {1359-7345}, doi = {10.1039/c3cc40541a}, author = {Philkhana, Satish Chandra and Seetharamsingh, B. and Dangat, Yuvraj B. and Vanka, Kumar and Reddy, D. Srinivasa} } @article { ISI:000364803200005, title = {Design, synthesis, and identification of silicon incorporated oxazolidinone antibiotics with improved brain exposure}, journal = {ACS Medicinal Chemistry Letters}, volume = {6}, number = {11}, year = {2015}, month = {NOV}, pages = {1105-1110}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

Therapeutic options for brain infections caused by pathogens with a reduced sensitivity to drugs are limited. Recent reports on the potential use of linezolid in treating brain infections prompted us to design novel compounds around this scaffold. Herein, we describe the design and synthesis of various oxazolidinone antibiotics with the incorporation of silicon. Our findings in preclinical species suggest that silicon incorporation is highly useful in improving brain exposures. Interestingly, three compounds from this series demonstrated up to a 30-fold higher brain/plasma ratio when compared to linezolid thereby indicating their therapeutic potential in brain associated disorders.

}, keywords = {Antibacterial, brain exposure, linezolid, oxazolidinone, sila analogue}, issn = {1948-5875}, doi = {10.1021/acsmedchemlett.5b00213}, author = {Seetharamsingh, B. and Ramesh, Remya and Dange, Santoshkumar S. and Khairnar, Pankaj V. and Singhal, Smita and Upadhyay, Dilip and Veeraraghavan, Sridhar and Viswanadha, Srikant and Vakkalanka, Swaroop and Reddy, D. Srinivasa} } @article { ISI:000352463200009, title = {Total synthesis and structural revision of mycalol, an anticancer natural product from the marine source}, journal = {Organic Letters}, volume = {17}, number = {7}, year = {2015}, month = {APR}, pages = {1652-1655}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

The total synthesis of an anticancer (anaplastic thyroid) natural lipid mycalol has been accomplished for the first time. Synthesis of originally proposed structure necessitated the revision of structure in which the position of acetate group moved from C20 to C19 and a change in stereochemistry of the glycerol unit.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.5b00345}, author = {Seetharamsingh, B. and Rajamohanan, P. R. and Reddy, D. Srinivasa} } @article { ISI:000367701900032, title = {First total synthesis of gliomasolide C and formal total synthesis of sch-725674}, journal = {Journal of Organic Chemistry}, volume = {81}, number = {1}, year = {2016}, month = {JAN}, pages = {290-296}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

Syntheses of two 14-membered macrolides Sch-725674 and Gliomasolide C are described here. The first total synthesis of Gliomasolide C, the short synthesis of Sch-725674, and regios elective Wacker oxidation of internal olefin are the highlights of this disclosure. In addition, a key macrocyde with orthogonal functionalities was designed and synthesized on a gram scale for the generation of analogues.

}, issn = {0022-3263}, doi = {10.1021/acs.joc.5b02318}, author = {Seetharamsingh, B. and Khairnar, Pankaj V. and Reddy, D. Srinivasa} } @article {43473, title = {Determination of the absolute configuration of gliomasolide D through total syntheses of the C-17 epimers}, journal = {Journal of Natural Products}, volume = {80}, year = {2017}, month = {FEB}, pages = {560-564}, abstract = {The absolute configuration at C-17, the carbon bearing the distal hydroxy group of the 14-membered natural product gliomasolide D, was assigned as R by comparison of C-13 NMR shifts and specific rotation values of the epimers at C-17. The first total synthesis of gliomasolide D along with its C-17 epimer, regioselective macrocyclization (18 membered vs 14 membered), and regioselective Wacker oxidation are highlights of the present work.}, doi = {10.1021/acs.jnatprod.6b00926}, author = {Seetharamsingh, B. and Ganesh, Routholla and Reddy, D. Srinivasa} } @article {43744, title = {Identification and synthesis of mycalol analogues with improved potency against anaplastic thyroid carcinonia cell lines}, journal = {Journal of Natural Products}, volume = {80}, year = {2017}, month = {APR}, pages = {1125-1133}, type = {Article}, abstract = {The marine metabolite mycalol (1) has a specific inhibitory activity on cells of anaplastic thyroid carcinoma (ATC), a very aggressive and rare cancer that does not have effective conventional therapy. In this study, we describe six new related analogues (2-7) that differ in the length of the terminal alkyl residue and the presence of acetate or 3S-hydroxybutyrate (3S)-3HB as a substituent at C-19. Despite the structural{\textquoteright} analogies, some of the new members were significantly more-cytotokic than 1 on cell lines,derivecl from human ATC. Structures inclusive of the 2{\textquoteright}R,3R,4S,7R,8S,19R absolute configuration were asigned to 2-7 on the basis of detailed spectroscopic analysis, synthesis of different isomers, and application of ECD and Mosher{\textquoteright}s methods. This work led to the identification of mycal61-578 (3) as the most potent analogue, with an IC50 of 2.3 mu M on FRO cells:}, doi = {10.1021/acs.jnatprod.7b00043}, author = {Cutignano, Adele and Seetharamsingh, B. and D{\textquoteright}Angelo, Daniela and Nuzzo, Genoveffa and Khairnar, Pankaj V. and Fusco, Alfredo and Reddy, D. Srinivasa and Fontana, Angelo} } @article {45594, title = {Insect-repellent and mosquitocidal effects of noreremophilane- and nardoaristolone-based compounds}, journal = {ACS Omega}, volume = {4}, year = {2019}, month = {JAN}, pages = {2188{\textendash}2195}, type = {Article}, abstract = {

Here, we disclose novel mosquito-repellent synthetic hydrindanes based on noreremophilanes and nardoaristolone B which show increased activity against adult females of Aedes aegypti. The noreremophilanes and nardoaristolone B with hydrindane skeleton are structurally related to nootkatone with decalin skeleton, a well-studied natural product extracted from a grape fruit. Out of our library of compounds synthesized based on the noreremophilanes and nardoaristolone B scaffolds, NDS-100598 (compound 20) exhibits higher repellent and knock-down effects at a very low concentration (0.25 mg/cm2), while a few analogues showed considerably enhanced activity compared to racemic nootkatone. This is the first report documenting insect-repellent and knock-down activity of the noreremophilanes class of compounds.

}, doi = {10.1021/acsomega.8b03652}, author = {Handore, K. L. and Kalmode, H. P. and Sayyad, S. and Seetharamsingh, B. and Gathalkar, G. and Padole, S. and Pawar, P. V. and Joseph, M. and Sen, A. and Reddy, D. S.} }