Organic Synthesis, Enantioselective Catalysis (Organocatalysis and Metal-based Catalysis) Natural Product Synthesis, Medicinal Chemistry

The development of expedient asymmetric routes to functionalized organic molecules is of interest because most chiral, biologically relevant molecules are optimally active as single enantiomers.

Our research interests are mainly in the area of asymmetric organic synthesis. We have developed organocatalytic variants of conjugate addition reactions and vinylogous aldol reactions, and we have applied our methodology in the total synthesis of a variety of alkaloids. We have also utilized ephedrine as a chiral controller in the asymmetric synthesis of alpha hydroxy acids and applied this methodology in the synthesis of alkaloids and marine natural products. Other synthetic methodologies developed in our group include new applications of sulfamide in the synthesis of vicinal diamines and related heterocycles and the hetero atom-H bond insertion reactions of diazocarbonyl compounds. We have identified scandium triflate as a promising catalyst for the insertion reactions.

Recent research in our group focuses on the design of new organocatalysts for fundamental, carbon-carbon bond forming reactions. We are also interested in the development of new multicomponent reactions for combinatorial chemistry based applications in diversity-oriented synthesis.

Current research projects include

• Asymmetric, organocatalytic carbon-carbon bond forming reactions, e.g. Michael, aldol and nitroaldol (Henry) reactions.
• Asymmetric synthesis of functionalized pyrrolidines, indolizidines and quinolizidines
• Asymmetric synthesis of substituted hydroxy amino acid motifs (peptide isosteres).
• Diazocarbonyl insertion reactions into C-H, N-H and O-H bonds.
• Synthesis of highly functionalized mono- and bicyclic scaffolds for diversity oriented synthesis.

Selected publications

Virk. S; Pansare, S. V.
Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II
Org. Lett. 2019, 21, 5524.

Muthusamy, G.; Pansare, S. V.
Stereoselective Synthesis of E-3-(Arylmethylidene)-5-(Alkyl/Aryl)-2(3H) Furanones by Sequential Hydroacyloxylation-Mizoroki–Heck Reactions of Iodoalkynes
Org. Biomol. Chem. 2018, 16, 7971.

Manchoju, A.; Annadate, R. A.; Desquien, L.; Pansare, S. V.
Functionalization of Diazotetronic Acid and Application in a Stereoselective Modular Synthesis of Pulvinone, Aspulvinones A–E, G, Q and their Analogues
Org. Biomol. Chem. 2018, 16, 6224.

Annadate, R. A.; N. V. G. Moorthy, Pansare, S. V.
Studies on the Organocatalytic Enantioselective Michael Addition of Cyclic Ketones and α,α-Disubstituted Aldehydes to α-Nitrostyrenes
Current Organocatalysis 2018, 5, 66. Open Access: www.eurekaselect.com/163073

N. V. G. Moorthy; Pansare, S. V.
Synthesis of the Diaryindolizidine Alkaloid (+)-Fistulopsine B. Application of an Organocatalytic Michael Addition Reaction
Tetrahedron 2018, 74, 1422.

Cooze, C.; Manchoju, A.; Pansare, S. V.
Synthesis of (–)-Muricatacin and (–)-(R,R)-L-Factor Involving an Organocatalytic Direct Vinylogous Aldol Reaction
Synlett 2017, 28, 2928. (Special issue in honor of Professor Victor Snieckus)

Manchoju, A.; Pansare, S. V.
Catalytic Undirected Intermolecular C−H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3‑Aryl Tetronic Acids,
Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate
Org. Lett. 2016, 18, 5952.

Gopinathan, M.; Pansare, S. V.
Modular Synthesis of Allyl Vinyl Ethers for the Enantioselective Construction of Functionalized Quaternary Stereocenters
RSC Adv. 2016, 6, 104556.

Moorthy, N. V. G.; Dyapa, R.; Pansare, S. V.
Formal Synthesis of (+)-Lasubine II and (-)-Subcosine II via Organocatalytic Michael Addition
of a Ketone to an alpha-Nitrostyrene
Org. Lett. 2015, 17, 5312.

Manchoju, A.; Thorat, R. G.; Pansare, S. V.
Enantioselective Synthesis of Functionalized Quaternary Stereocenters
Eur. J. Org. Chem. 2015, 5939.

Pansare, S. V.; Thorat, R. G.
Recent Advances in the Synthesis of Selected Indolizidine and Quinolizidine Alkaloids
Targets in Heterocyclic Systems 2013, 17, 57.

Thorat, R. G.; Pansare, S. V.
A General Approach to 1-Hydroxymethylquinolizidine and
8-Hydroxymethylindolizidine Stereoisomers: Synthesis of (+)-Epitashiromine and Formal Syntheses of (+)-Epilupinine and (+)-Tashiromine Eur. J. Org. Chem. 2013, 7282.

Pansare, S. V.; Kulkarni, K. G.
An enantioselective approach to (-)-aphanorphine featuring a stereoselective oxidative amidation RSC Advances 2013, 3, 19127.

Pansare, S. V.; Paul, E. K.
Synthesis of Synthesis of (+)-Febrifugine and a Formal Synthesis of (+)-Halofuginone Employing an Organocatalytic Direct Vinylogous Aldol Reaction
Synthesis 2013, 45, 1863. (Special issue in honor of Professor Scott Denmark)
(Featured on the Organic Chemistry portal (www.organic-chemistry.org/Highlights/2014/12May.shtm)

Pansare, S. V.; Dyapa, R.
Enantioselective Approach to Functionalized Quinolizidines: Synthesis of (+)-Julandine and (+)-Cryptopleurine
Org. Biomol. Chem. 2012, 10, 6776.

Pansare, S. V.; Paul, E. K.
Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-Hydroxypipecolic acid: Application of an Organocatalytic direct vinylogous aldol reaction
Org. Biomol. Chem. 2012, 10, 2119.

Pansare, S. V.; Paul, E. K.
The Organocatalytic Vinylogous Aldol Reaction: Recent Advances
Chem. Eur. J. 2011, 17, 8770.
(Among the top 20 most cited Minireviews in 'Chemistry—A European Journal' in the past 20 years)

Pansare, S. V.; Lingampally, R.; Dyapa, R.
A Simple Enantioselective Route to Functionalized Indolizidines: Synthesis of (+)-Ipalbidine and (+)-Antofine
Eur. J. Org. Chem. 2011, 2235.

Pansare, S. V.; Paul, E. K.
Organocatalytic Asymmetric Direct Vinylogous Aldol Reactions of g-Crotonolactone with Aromatic Aldehydes
Chem. Commun. 2011, 47, 1027.

Pansare, S. V.; Adsool, S. V.; Dyapa, R.
Enantioselective Synthesis of (S) - Homocitric Acid Lactone and (R) - Per Homocitric Acid Lactone Involving Organocatalysis
Tetrahedron: Asymmetry 2010, 21, 771.

Pansare, S. V.; Lingampally, R.; Kirby, R. L.
Stereoselective Synthesis of 3-Aryloctahydroindoles and Application in a Formal Synthesis of (-)-Pancracine
Org. Lett. 2010, 12, 556.
(Highlighted in Synfacts 2010, 3, 354)

Pansare, S. V.; Kirby, R. L.
Secondary-Secondary Diamine Catalysts for the Enantioselective Michael Addition of Cyclic Ketones to Nitroalkenes
Tetrahedron 2009, 65, 4557.

Pansare, S. V.; Lingampally, R.
Synthesis and Evaluation of Guanidinyl Pyrrolidines as Bifunctional Catalysts
for Enantioselective Conjugate Additions to Cyclic Enones
Org. Biomol. Chem. 2009, 7, 319.
(In OBC Top 10 articles, January 2009)

Adsool, V. A.; Pansare, S. V.
An Enantioselective Approach to (+)-Laurencin
Org. Biomol. Chem. 2008, 6, 2011.

Pansare, S. V.; Adsool, V. A.
Enantioselective Synthesis of (R)-Homocitric Acid Lactone
Tetrahedron Lett. 2007, 48, 7099.

Pansare, S. V.; Adsool, V. A.
Enantioselective Synthesis of Functionalized Medium-Sized Oxacycles
Org. Lett. 2006, 8, 5897.

Pansare, S. V.; Pandya, K.
Simple Diamine- and Triamine-Protonic Acid Catalysts for the Enantioselective
Michael Addition of Cyclic Ketones to Nitroalkenes
J. Am. Chem. Soc. 2006, 128, 9624.
(JACS Hot Paper, May 2007)

Pansare, S. V.; Adsool, V. A.
A Concise, Enantioselective Approach to (-)-Quinic Acid
Org. Lett. 2006, 8, 2035.