Asymmetric Synthesis Laboratory

Department of Chemistry

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Publications and Patents :

[IIT Bombay]

2014

[70] Iron(III) Sulfate as Terminal Oxidant in the Synthesis of Methyl Ketones via Wacker Type Oxidation.
Rodney A. Fernandes* and Dipali A. Chaudhari, J. Org. Chem. 2014, 79, 5787?5793.

[69] Tandem Benzylic Oxidative Dihydroxylation of α-Vinyl and α-Alkenylbenzyl Alcohols.
Rodney A. Fernandes* and Pullaiah Kattanguru, Helv. Chim. Acta 2014.

[68] Synthesis of Methyl Ketones from Terminal Olefins using PdCl2/CrO3 System Mimicking the Wacker Process.
Rodney A. Fernandes* and Venkati Bethi, Tetrahedron 2014, 70, 4760.

[67] The Chiral Cups (Calixarenes) via Dötz Benzannulation.
Rodney A. Fernandes* and Sandip V. Mulay Synthesis 2014, 46, 1836-1846 .

[66] A Practical and Improved Process for the Synthesis of Hagen's Gland Lactones by Catalytic Hydro-deiodination.
Dipali A. Chaudhari, Pullaiah Kattanguru and Rodney A. Fernandes* Tetrahedron: Asymmetry 2014, 25, 1022-1025.

[65] Domino Recombinant γ-Isomerization and Reverse Wacker Oxidation of γ-Vinyl-γ-butyrolactone: Synthesis of (+)-trans-, (-)- and (+)-Disparlures.
Venkati Bethi, Pullaiah Kattanguru and Rodney A. Fernandes* Eur. J. Org. Chem. 2014, 3249.

[64] Stereoselective inversion of γ-vinyl-γ-butyrolactone under palladium catalysis: Application to the synthesis of (+)-exo- and (+)-endo-brevicomins.
Rodney A. Fernandes,* Pullaiah Kattanguru and Venkati Bethi, RSCAdv. 2014, 4, 14507.

[63] A Facile ChemoselectiveDeprotection of Aryl Silyl Ethers using Sodium Hydride/DMF and in situ Protection of Phenol with Various Groups.
Rodney A. Fernandes,* Sachin P. Gholap and Sandip V. Mulay, RSCAdv. 2014, 4, 16438.

[62] Ring-Closing Metathesis Enabled Efficient Synthesis of g-Butenolide Antifungal Agent (-)-Incrustoporin and its Analogues.
Rodney A. Fernandes, Pradnya H. Patil, Asim K. Chowdhury, Asian. J. Org.Chem. 2014, 58.

[61] The Orthoester Johnson-Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates - Recent Advances
Rodney A. Fernandes, Asim K. Chowdhury, Pullaiah Kattanguru, Eur. J. Org. Chem. 2014, 2833.

2013

[60] A Late Stage b-Epimerization: A Stereodivergent to Stereoconvergent Relay to the First Total Synthesis of (+)-Murolic Acid.
Rodney A. Fernandes, Pradnya H. Patil, Asim K. Chowdhury, Eur. J. Org. Chem. 2013, 237.

[59] A concise total synthesis of arizonins B1 and C1.
Rodney A. Fernandes, Sandip V. Mulay, Vijay P. Chavan Tetrahedron: Asymmetry 2013, 24, 1548.
(highlighted in ChemInform Abstract) Link

[58] A Highly Diastereoselective Oxa-Pictet-Spengler approach to (+)-Astropaquinone B and (+)-Astropaquinone C and the Formation of Astropaquinone B Dimer
Rodney A. Fernandes, Sandip V. Mulay, Tetrahedron: Asymmetry 2013, 24, 1281.
(highlighted in ChemInform Abstract) - Link

[57] Total Synthesis of Both Spiroketal Diastereomers of the Reported Structure of Cephalosporolide H.
Rodney A. Fernandes, Mahesh B. Halle, Asian J. Org. Chem. 2013,7, 593 , Editor's Choice articles when accepted.
(Highlighted in CHEMISTRY VIEWS as "Cephalosporolide H gives up more of its structural secrets" on 24th June 2013)    Link
.

[56] A Synthesis of (R)-(-)-and (S)-(+)-Lavandulol, (+)-Lavandulyl-2-methylbutanoate and (+)-Lavandulyl Senecioate through Orthoester Johnson-Claisen Rearrangement.
Rodney A. Fernandes, Asim K. Chowdhury, Eur. J. Org. Chem. 2013, 5165.

[55] A 12-Membered to a Strained 11-Membered Ring: First Stereoselective Total Synthesis of ()-Asteriscunolide C.
Rodney A. Fernandes and Vijay P. Chavan. Chem. Commun. 2013, 49, 3354.

[54] Arundic Acid a Potantial Neuroprotective Agent: Biological Development and Syntheses.
Rodney A. Fernandes and Arun B. Ingle. Curr. Med. Chem. 2013, 20, 2315.

[53] Step Economic and Protecting-Group-Free Total Synthesis of (+)-Cardiobutanolide.
Rodney A. Fernandes and Pullaiah Kattanguru. Asian J. Org. Chem. 2013, 2, 74. Featured Article (Most accessed article upto August 2013)

2012

[52] A Chiron Approach to the Total Synthesis of (-)-Juglomycin A, (+)-Kalafungin, (+)-Frenolicin B and (+)-Deoxyfrenolicin.
Rodney A. Fernandes, Vijay P. Chavan, Sandip V. Mulay, Amarender Manchoju. J. Org. Chem. 2012, 77, 10455.

[51] A Protecting-Group-Free Synthesis of Hagen's Gland Lactones
Rodney A. Fernandes, Pullaiah Kattanguru. J. Org. Chem. 2012, 77, 9357.

[50] Enantioselective allylation of imines catalyzed by newly developed (-)-beta-pinene-based pi-allylpalladium catalyst: an efficient synthesis of (R)-alpha-propylpiperonylamine and (R)-pipecolic acid
Rodney A. Fernandes and Jothi L. Nallasivam. Org. Biomol. Chem. 2012, 10, 7789.

[49] Stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3
Rodney A. Fernandes, Arun B. Ingle and Vijay P. Chavan. Org. Biomol. Chem. 2012,10, 4462

[48] Development of first menthane based chiral pi-allylpalladium catalysis: asymmetric allylation of imines Rodney A. Fernandes, Dipali A. Chaudhari. Eur. J. Org. Chem. 2012, 1945.

[47] A control of diastereoselectivity in orthoester Johnson-Claisen rearrangement of tartrate based allyl alcohol: a efficient synthesis of Alzheimer's potential therapeutic agent, arundic acid.
Rodney A Fernandes, Arun B Ingle, Dipali A. Chaudhari. Eur. J. Org. Chem. 2012, 1047

[46] Diatereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid
Rodney A. Fernandes, Mahesh B. Halle, Asim K. Chowdhury, Arun B. Ingle. Tetrahedron: Asymmetry 2012, 23, 60

[45] A novel process for the four step protecting group free synthesis of (+)-Hagen's gland lactones. Provisional Indian process patent application filed, No. 1908/MUM/2012.
Rodney A. Fernandes and Pullaiah Kattanguru.

[44] Process for the three step synthesis of (+)-cardiobutanolide from D-glucono-?-lactone. Provisional Indian process patent application filed, No. 1780/MUM/2012.
Rodney A. Fernandes and Pullaiah Kattanguru.



2011

[43] Total synthesis of (8S,11R,12R)- and (8R,11R,12R)-topsentolide B2 diastereomers and assignment of absolute configuration.
Rodney A. Fernandes, Pullaiah Kattanguru. Tetrahedron:Asymmetry 2011 22, 1930-1935

[42] A concise stereoselective synthesis of tetracyclic naphthoquinone, (-)-isagarin.
Rodney A. Fernandes, Arun B. Ingle. Eur. J. Org. Chem. 2011, 6624-6627

[41] A Dötz benzannulation route to the enantioselective synthesis of (-) and (+)-juglomycin A.
Rodney A. Fernandes, Vijay P. Chavan, Tetrahedron:Asymmetry 2011, 22, 1312.

[40] A concise synthesis of paraconic acids: (-)-methylenolactocin and (-)-phaseolinic acid.
Rodney A. Fernandes, Asim K. Chowdhury, Tetrahedron:Asymmetry 2011, 22, 1114.

[39] A concise and improved synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B.
Rodney A. Fernandes, Vijay P. Chavan, Sandip V. Mulay, Tetrahedron:Asymmetry 2011, 22, 487-492.

[38] Total synthesis of topsentolide B2.
Rodney A. Fernandes, Pullaiah Katanguru, Tetrahedron Letters 2011, 52, 1788.

[37]Stereoselective Total Synthesis of (+)-Nephrosteranic Acid and (+)-Roccellaric Acid through Asymmetric Dihydroxylation and Johnson-Claisen Rearrangement.
Rodney A. Fernandes, Asim K. Chowdhury, Eur. J. Org. Chem. 2011, 1106.

[36]Synthetic studies on C14 cembranoids: synthesis of C412 fragment of sarcophytonolides EG and L and C511 fragment of sarcophytonolide L.
Rodney A. Fernandes, Arun B. Ingle, Tetrahedron Letters 2011, 52, 458.

2010

[35] Total synthesis of (+)-demethoxycardinalin 3.
Rodney A. Fernandes, Sandip V. Mulay, J. Org. Chem. 2010, 75, 7029.

[34] Dimeric Fischer carbenes: a bidirectional Dötz benzannulation approach to the synthesis of regioisomeric core of cardinalin 3.
Rodney A. Fernandes, Sandip V. Mulay, Synlett 2010, 2667.

[33] A Concise Asymmetric Synthesis of (-)-Hongconin and (-)-1-epi-Hongconin.
Rodney A. Fernandes, Vijay P. Chavan, Eur. J. Org. Chem. 2010, 4306.

[32] Total Synthesis of (+)-Cephalosporolide E and (-)-Cephalosporolide F en route to Bassianolone.
Rodney A. Fernandes, Arun B. Ingle, Synlett 2010, 158.


2009

[31] Synthesis of chiral beta,gamma-disubstituted-gamma-lactones through Johnson-Claisen rearrangement: A short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolides.
Rodney A. Fernandes, Arun B. Ingle, Vijay P. Chavan, Tetrahedran : Asymmetry 2009, 20, 2835.

[30] Total Syntheses of all Stereoisomers of Phenatic Acid B.
Rodney A. Fernandes, Asim K. Chowdhury, J. Org. Chem. 2009, 74, 8826.

[29] A Diethyltartrate-based Synthesis of both (+)- and (-)-Arundic Acid.
Rodney A. Fernandes, Abhinav Dhall, Arun B. Ingle, Tetrahedron Lett. 2009, 50, 5903.

[28] Chiral Vicinal Diols as Platforms for Separable Diastereomers in Johnson-Claisen Rearrangement: A New Short Route to (-)-Nor-canadensolide, (-)-Canadensolide and (-)-Sporothriolide.
Rodney A. Fernandes, Arun B. Ingle, Tetrahedron Lett. 2009, 50, 1122.


2008

[27] A Short Enantioselective Synthesis of (+)-Eleutherin, (+)-Allo-eleutherin and a Formal Synthesis of (+)-Nocardione B.
Rodney A. Fernandes, Vijay P. Chavan, Arun B. Ingle, Tetrahedron Lett. 2008, 49, 6341.

[26] A Highly Enantioselective Synthesis of (-)- and (+)-Juglomycin A through Dötz Annulation and Asymmetric Dihydroxylation.
Rodney A. Fernandes, Vijay P. Chavan, Tetrahedron Lett. 2008, 49, 3899.



[Institute of Chemistry, UNAM, Mexico]

[25] A Short Synthesis of (+)-(S)-Kurasoin B.
Rodney A. Fernandes, Tetrahedron: Asymmetry 2008, 19, 15.

[24] An Efficient Synthesis of (-)-Posticlure: The Sex Pheromone of Orygia Postica.
Rodney A. Fernandes, Eur. J. Org. Chem. 2007, 5064.



[Alexander von Humboldt Fellow, Freiburg University, Freiburg, Germany]

[23] First synthesis of the pyrano-naphthoquinone lactone (-)-arizonin C. [Cover Page Article]
Manuel Mahlau, Rodney A. Fernandes, Reinhard Brückner, Eur. J. Org. Chem. 2011, 4765 4772.

[22] Efficient synthesis of (+)-kalafungin and (-)-nanaomycin by asymmetric dihydroxylation, oxa-Pictet-Spengler cyclization, and H2SO4-mediated isomerization.
Rodney A. Fernandes, Reinhard Brückner, Synlett 2005, 1281.



[Tohoku University, Sendai, Japan]

[21] Catalytic asymmetric carbalkoxyallylation of imines with chiral bis-π-allylpalladium complex.
Rodney A. Fernandes, Yoshinori Yamamoto, J. Org. Chem. 2004, 69, 3562.

[20] Catalytic asymmetric allylation of imines with Tetraallylsilane-TBAF-MeOH system using bis-π-allyl palladium complex. Japanese patent JP 2003-396110, 2003.
Yoshinori Yamamoto and Rodney A. Fernandes.

[19] The first catalytic asymmetric allylation of imines with tetraallylsilane-TBAF-MeOH system using chiral bis-π-allylpalladium complex.
Rodney A. Fernandes, Yoshinori Yamamoto, J. Org. Chem. 2004, 69, 735.

[18] Chiral bis-π-allylpalladium catalyzed allylation of imines: Enhancement of chemical yield and enantioselectivity by water.
Rodney A. Fernandes, Anton Stimac, Yoshinori Yamamoto, J. Am. Chem. Soc. 2003, 125, 14133.

[17] Preparation of bis-π-allyl palladium complex and synthetic procedure for asymmetric allylamines. Japanese patent JP 2003-358265, 2003.
Yoshinori Yamamoto, Rodney A. Fernandes and Anton Stimac.



[National Chemical Laboratory, Pune]

[16] An asymmetric dihydroxylation route to (R)-(-)-octopamine, (R)-(-)-tembamide and (R)-(-)-aegeline.
Sadyandi Ramalingam, Rodney A. Fernandes, Pradeep Kumar, Arkivoc 2005, (iii) 36 43.

[15] An improved process for the preparation of enantiomerically pure cyclohexylphenyl glycolic acid, US patent, No. 6825378, 2004.
Pradeep Kumar, Rodney A. Fernandes and Priti Gupta.

[14] PCC: Novel oxidation reactions.
Rodney A. Fernandes, Synlett Spotlight 2003, 741 742.

[13] An asymmetric dihydroxylation route to (S) oxybutynin.
Priti Gupta, Rodney A. Fernandes, Pradeep Kumar, Tetrahedron Letters 2003, 44, 4231 4232.

[12] A new PCC mediated oxidation reaction of homobenzylic and homoallylic alcohols.
Rodney A. Fernandes, Pradeep Kumar, Tetrahedron Letters 2003, 44, 1275 1278.

[11] Enantioselective synthesis of xylo C18 phytosphingosines using double stereodifferentiation.
Rodney A. Fernandes, Pradeep Kumar, Synthesis 2003, 129 135.

[10] A concise synthesis of (+) compactin lactone via asymmetric dihydroxylation and regioselective cyclic sulfite opening reactions.
Rodney A. Fernandes, Pradeep Kumar, Eur. J. Org. Chem. 2002, 2921 2923.

[9] Asymmetric dihydroxylation and one-pot epoxidation routes to (+) and (-) posticlure: A novel trans-epoxide as a sex pheromone component of Orgyia postica (Walker).
Rodney A. Fernandes, Pradeep Kumar, Tetrahedron 2002, 58, 6685 6690.

[8] An asymmetric dihydroxylation route to enantomerically pure norfluoxetine and fluoxetine.
Rajesh Kumar Pandey, Rodney A. Fernandes, Pradeep Kumar, Tetrahedron Letters 2002, 43, 4425 4426.

[7] Asymmetric dihydroxylation and regioselective C-3 indole coupling routes to the anticoccidial antibiotic (+) diolmycin A2.
Rodney A. Fernandes, Mandar S. Bodas, Pradeep Kumar, Tetrahedron 2002, 58, 1223 1227.

[6] An improved process for the preparation of (4R,6S)-4-Hydroxy-6-hydroxymethyl- tetrahydro-pyran-2-one, US Patent, No 6376683, 2002.
Pradeep Kumar and Rodney A. Fernandes.

[5] Double stereodifferentiation in asymmetric dihydroxylation: Application to the first diastereoselective synthesis of L xylo [2R,3S,4S] C18 phytosphingosine.
Rodney A. Fernandes, Pradeep Kumar, Tetrahedron Letters 2000, 41, 10309 10312.

[4] A stereoselective synthesis of dihydrosphingosine.
Rodney A. Fernandes, Pradeep Kumar, Eur. J. Org. Chem. 2000, 3447 3449.

[3] A short and efficient stereoselective synthesis of dihydrosphingosine triacetate.
Rodney A. Fernandes, Pradeep Kumar, Tetrahedron: Asymmetry 1999, 10, 4797 4802.

[2] Enantioselective synthesis of (R) ( ) mevalonolactone via cylcic sulfate methodology.
Rodney A. Fernandes, Pradeep Kumar, Tetrahedron: Asymmetry 1999, 10, 4349 4356.

[1] Asymmetric synthesis of (S) massoialactone.
Godwin C. G. Pais, Rodney A. Fernandes, Pradeep Kumar, Tetrahedron 1999, 55, 13445 13450.