@article { ISI:000302810800004, title = {Green synthetic route to antimalarial and antibacterial agent CJ-15,801 and its isomer cis-CJ-15,801}, journal = {RSC Advances}, volume = {2}, number = {9}, year = {2012}, month = {MAR}, pages = {3596-3598}, publisher = {ROYAL SOC CHEMISTRY}, type = {Article}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

An efficient and rapid synthesis of antiplasmodial and antibacterial agent CJ-15,801 and its isomer cis-CJ-15,801 is disclosed. We have made an attempt towards {\textquoteleft}{\textquoteleft}Ideal Synthesis{\textquoteright}{\textquoteright} or a step towards {\textquoteleft}{\textquoteleft}Dial-a-Molecule{\textquoteright}{\textquoteright} by reducing the number of steps, following atom economy, and a green synthetic route.

}, issn = {2046-2069}, doi = {10.1039/c2ra01051h}, author = {Kashinath, K. and Swaroop, Pandrangi Siva and Reddy, D. Srinivasa} } @article { ISI:000312564500027, title = {Studies toward the synthesis of potent anti-inflammatory peptides solomonamides A and B: synthesis of a macrocyclic skeleton and key fragment 4-amino-6-(2 {\textquoteleft}-amino-4 {\textquoteleft}-hydroxyphenyl)-3-hydroxy-2-methyl-6-oxohexanoic acid (AHMOA)}, journal = {Organic Letters}, volume = {14}, number = {24}, year = {2012}, month = {DEC}, pages = {6222-6225}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

A first synthetic effort toward total synthesis of highly potent solomonamides is disclosed. An efficient strategy to synthesize this class of compounds, along with the synthesis of a core macrocycle (shown in red) and the key fragment AHMOA, is described.

}, issn = {1523-7060}, doi = {10.1021/ol303149k}, author = {Kashinath, K. and Vasudevan, N. and Reddy, D. Srinivasa} } @article { ISI:000336844400011, title = {Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus flammulina velutipes}, journal = {Organic \& Biomolecular Chemistry}, volume = {12}, number = {24}, year = {2014}, month = {APR}, pages = {4098-4103}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

The first total synthesis of a norsesquiterpene alkaloid (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclo-penta[e]isoindole-1,3(2 H,6H)-dione, isolated from the mushroom-forming fungus Flammulina velutipes, in both racemic and enantiomeric pure forms, is reported. The (-)-enantiomer of the natural product has been synthesized from the D-(-)-pantolactone chiral pool. The synthesis features a one-pot, three-step reaction sequence comprising an enyne RCM/Diels-Alder/aromatization to construct the desired indane skeleton present in the natural product. Our synthesis further confirms the assigned structure and absolute configuration of the natural product.

}, issn = {1477-0520}, doi = {10.1039/c4ob00300d}, author = {Kashinath, K. and Jadhav, Prakash D. and Reddy, D. Srinivasa} } @article { ISI:000346037500028, title = {Total synthesis of deoxy-solomonamide B by mimicking biogenesis}, journal = {Organic Letters}, volume = {16}, number = {23}, year = {2014}, month = {DEC}, pages = {6148-6151}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

A total synthesis of Deoxy-solomonamide B was accomplished starting from tryptophan in an efficient manner by mimicking the proposed biogenetic route. The present synthesis utilizes a crotylation, oxidative cleavage of the indole moiety, and macrolactamization as key steps. The use of the indole nucleus as a masked anthranilic acid unit paves the way for the easy synthesis of related macrocycles and natural products where the ortho-acyl aniline moiety is embedded into them, which otherwise is difficult to synthesize.

}, issn = {1523-7060}, doi = {10.1021/ol503011g}, author = {Vasudevan, N. and Kashinath, K. and Reddy, D. Srinivasa} } @article { ISI:000354004400014, title = {Breaking and making of olefins simultaneously using ozonolysis: application to the synthesis of useful building blocks and macrocyclic core of solomonamides}, journal = {Organic Letters}, volume = {17}, number = {9}, year = {2015}, month = {MAY}, pages = {2090-2093}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

A simple and practical one-pot) two-directional approach to access olefinic esters through simultaneous breaking and making of olefins using ozonolysis of alkenyl aryl selenides is disclosed The scope of the method with a variety of example{\textquoteright}s is demonstrated, and the end products obtained here are useful building blocks. As a direct application of the present method,the macrocyclic cote of potent anti-inflammatory natural cyclic peptides, solomonamides, is synthesized.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.5b00637}, author = {Kashinath, K. and Dhara, Santu and Reddy, D. Srinivasa} } @article { ISI:000347229500001, title = {One-pot quadruple/triple reaction sequence: a useful tool for the synthesis of natural products}, journal = {Organic \& Biomolecular Chemistry}, volume = {13}, number = {4}, year = {2015}, month = {OCT}, pages = {970-973}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Multiple reactions in one pot has always been a useful technique for synthetic organic chemists, as it can minimizes solvent usage, time and the number of purification steps when compared to individual multi-step syntheses. In line with this, here in this perspective we discuss a one-pot quadruple/triple reaction sequence comprising an enyne ring-closing metathesis/cross-metathesis/Diels-Alder/aromatization for the synthesis of natural products setting.

}, issn = {1477-0520}, doi = {10.1039/c4ob02143f}, author = {Kashinath, K. and Reddy, D. Srinivasa} } @article {42902, title = {Enantiospecific formal synthesis of inthomycin C}, journal = {Chemistry Select}, volume = {1}, year = {2016}, month = {MAR}, pages = {495{\textendash}497}, abstract = {

An enantiospecific synthesis of Hatakeyama{\textquoteright}s intermediate enynol has been accomplished in both enantiomeric forms. As these intermediates can be converted to (3R)-inthomycin C and (3S)-inthomycin C through respective enynol intermediates using reported procedures, present effort may be regarded as formal synthesis of inthomycin C in both enantiomeric forms. Our synthesis highlights the use of pantolactone chiral pool and thus reconfirms the previously assigned absolute stereochemistry as 3R to the natural product inthomycin C.

}, doi = {10.1002/slct.201600128}, author = {Athawale, Paresh R. and Kashinath, K. and Reddy, D. Srinivasa} } @article { ISI:000379577800033, title = {Molecules with O-acetyl group protect protein glycation by acetylating lysine residues}, journal = {RSC Advances}, volume = {6}, number = {70}, year = {2016}, month = {JUL}, pages = {65572-65578}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Pharmaceutical intervention for reduction of advanced glycation end products (AGEs) is considered as a therapeutic strategy to attenuate the pathogenesis of diabetes. Many molecules have been reported to possess antiglycation activity, one such example is acetylsalicylic acid (aspirin). It protects proteins from glycation by acetylating the lysine residues. Therefore, in this study we have synthesized and screened molecules containing free N-acetyl, O-acetyl and acetophenone groups. All the selected molecules in this study showed glycation inhibition but interestingly, only molecules with O-acetyl but not N-acetyl and acetophenone groups were capable of acetylating lysine residue. Furthermore, we have demonstrated that pre-acetylation or aspirin treatment prior to the induction of diabetes helps in reducing HbA1c and AGE formation in the streptozotocin induced diabetic mice. Hence pre-acetylation may have an additional therapeutic efficacy of reducing AGE levels in vivo. Incorporation of O-acetyl group into anti-diabetic molecules could be a useful strategy, as it may have an additive effect in reducing AGEs. Identification of such novel acetylating agents represents a new area in the drug discovery process.

}, issn = {2046-2069}, doi = {10.1039/c6ra11313c}, author = {Vannuruswamy, Garikapati and Jagadeeshaprasad, Mashanipalya G. and Kashinath, K. and Kesavan, Suresh K. and Bhat, Shweta and Korwar, Arvind M. and Chougale, Ashok D. and Boppana, Ramanamurthy and Reddy, D. Srinivasa and Kulkarni, Mahesh J.} } @article { ISI:000379455300035, title = {Total synthesis of the marine natural product solomonamide B necessitates stereochemical revision}, journal = {Organic Letters}, volume = {18}, number = {13}, year = {2016}, month = {JUL}, pages = {3178-3181}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

The first total synthesis of the proposed structure of solomonamide B has been achieved. However, the H-1 and C-13 NMR spectral data of the synthesized compound was not exactly matching with that of the natural solomonamide B. This prompted us to revise the originally proposed structure, in particular, the stereochemistry of the nonpeptide part, which was confirmed by its total synthesis. During the course of the synthesis, we have developed an interesting hydroxy group directed Wacker oxidation of internal olefins in a macrocyclic setting.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.6b01395}, author = {Kashinath, K. and Jachak, Gorakhnath R. and Athawale, Paresh R. and Marelli, Udaya Kiran and Gonnade, Rajesh G. and Reddy, D. Srinivasa} } @article {46324, title = {Access to a stereoisomer library of solomonamide macrocycles}, journal = {Chemistry-An Asian Journal}, year = {2019}, month = {OCT}, type = {Article; Early Access}, abstract = {

In an attempt towards understanding stereo-structure activity relationships (SSARs), we have prepared eight possible stereoisomers of solomonamide macrocycles, in particular, by changing the stereochemical pattern of non-peptide fragment AHMOA. Here, we have demonstrated different ways to construct three contiguous chiral centers present in solomonamide B macrocycle using substrate/reagent-controlled methods. These methods involve Brown crotylation, NHK reaction and Evans aldol addition as key steps to synthesize key non-peptide fragment. Further, these non-peptide fragments were converted to their corresponding macrocycles via ligand-free intramolecular Heck reaction.

}, keywords = {Crotylation, Heck reaction, Inflammation, Macrocycles, Stereochemistry}, issn = {1861-4728}, doi = {10.1002/asia.201901075}, author = {Jachak, Gorakhnath R. and Athawale, Paresh R. and Choudhury, Rahul and Kashinath, K. and Reddy, D. Srinivasa} }