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Total Synthesis of Natural Products

SN's Lab at IIT-KGP

PUBLICATIONS

Academic Publications from IIT-KGP

85. Asymmetric Total Synthesis of Naturally Occurring (−)-EBC-329 through an (E)-Selective Cross-Metathesis Reaction. Ghosh, S.; Sau, D and Nanda. S. J. Org. Chem. 2026 (https://doi.org/10.1021/acs.joc.6c00931)

EBC 329.tif

84. Synthetic studies towards Hamigeromycins A, B and E and total synthesis of 5'-epi-Caryospomycin C and Hyalodendriellin A. Das, J. and Nanda. S. Org. Biomol. Chem. 2026, 24, 6012 - 6020. DOI: 10.1039/D6OB00889E

Hamige A-E.tif

83. An isocoumarin route to resorcylic acid lactones (RALs): Asymmetric total synthesis of neocosmosin A, fusariumin and penicipyran D". Mandal, K. K and Nanda, S. Org. Biomol. Chem. 2026, 24, 2324-2331. DOI: https://doi.org/10.1039/D6OB00143B

untitled.tif

82. "Asymmetric total synthesis of (+)-Fusariumin and (+)-Sporotricale methyl ether: Exploration of Cu(I) catalysed regiodivergent cascade cyclization strategy". Das, S.; Karmakar, A.; Nanda, S. Org. Biomol. Chem. 2025, 23, 8282-8290. DOI: https://doi.org/10.1039/D5OB01245G

obc image.tif

81. "Total synthesis of few naturally occurring isocoumarins and dihydro-isocoumarins: Successful exploration of Ag(I) mediated 6-endo-dig cyclization and asymmetric hydrogenation strategy". Mandal, K. K.; Das, S.; Nanda, S. J. Org. Chem. 2025, 90, 4725–4734

JOC image.tif

80. "Synthetic studies towards naturally occurring sesquiterpene capillosanane V: Construction of fully functionalized cycloheptane core through intramolecular Reformatsky reaction". Barik, R.; Das, J.; Nanda, S. Org. Biomol. Chem. 2025, 23, 1696 - 1707.

capilisonanane.tif

79. "Protecting-Group Free Total Synthesis of β-Levantenolide through Late Stage Bromo-Spirocyclization". Ghosh, S.; Chatterjee, S.; Nanda, S. Org. Lett. 2024, 26, 49, 10453–10457.

OL TOC.tif

78. "Synthetic studies towards naturally occurring aporpinones: Asymmetric synthesis of 1'-deshydroxymethyl analogues of aporpinone A, aporpinone B and 4'-hydroxyaporpinone A". Mandal, K. K.; Das, S.; Nanda, S. Org. Biomol. Chem, 2024, 22, 9242-9248. DOI: 10.1039/D4OB01517G.

OBC TIF.tif

77. "Asymmetric total synthesis of naturally occurring (R)-2'-methoxydihydroartemidin, (R)-(E)-3'-hydroxyartemidin and its structural congeners: Method optimization and mechanistic analysis". Das, S.; Paul, S.; Mandal, K. K.; Anoop. A.; Nanda, S. J. Org. Chem, 2024, 89, 21, 15764-15776. https://doi.org/10.1021/acs.joc.4c01868.

JOC.tif

76. "Synthetic studies towards volvalerenol A: Access of fully functionalized cycloheptane framework in asymmetric fashion through the exploitation of C2-symmetry". Sahu, R. K.; Ghosh, S.; Bhatta, S.; Bisui, S.; Nanda,S. Org. Biomol. Chem. 2024, 22, 8163 - 8172.

volvalerenol A.tif

75. "Asymmetric synthesis of the fully functionalized cyclodecene core of naturally occurring sesquiterpene Hypocoprins A-C". Soni, K. C.; Mandal, K.; Sarkar, R.; Nanda, S. Tetrahedron, 2024, 163, 134143.

hypocoprin.tif

74. "Chemoenzymatic Asymmetric Total Synthesis of Naturally Occurring Resorcylic Acid Lactones Hamigeromycins F-G". Das, J.; Sarkar, R.; Nanda, S. Org. Biomol. Chem. 2024, 22, 5205-5213.

obc image.tif

73. "Synthetic studies towards naturally occurring bicyclic γ-alkylidene butenolide cochinolide through hetero Pauson-Khand reaction". Chatterjee, S.; Bisui, S.; Nanda, S. Tetrahedron, 2024, 160, 134029.

cochinolide TIF.tif

72. "Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, F and 2,9-humuladien-6-ol-8-one". Barik, R.; Nanda, S. Org. Biomol. Chem, 2024, 22, 4478-4487

toc.tif

71. "A Sequential Friedländer and anionic benzannulation strategy for the regiodefined assembly of unsymmetrical acridines". , Bhatta, S.; Senapati, B.; Patra, S.; and Nanda, S. Org. Biomol. Chem, 2023 ,21, 8727-8738.

TOC OBC.tif

70. "Synthetic studies towards naturally occurring γ-(Z)/(E)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method". Chatterjee, S.; Acharyya, R.; Pal, P and Nanda, S. Org. Biomol. Chem, 2022, 20, 2473-2499.

photoiosmerization.tif

69. Cyclobutane based “overbred intermediates” and their exploration in organic synthesis. Nandy, M.; Das, S and Nanda, S. Org. Biomol. Chem, 2022, 20, 1582-1622.

overbred.tif

68. Recent reports on the synthesis of γ-butenolide, γ-alkylidenebutenolide frameworks, and related natural products. Chatterjee, S.; Sahoo, R and Nanda, S. Org. Biomol. Chem, 2021, 19, 7298-7332.

OBC rev.tif

67. Stereoselective synthesis of novel carbocyclic and heterocyclic scaffolds of medicinal importance from biocatalytically derived enantiopure α-substituted-β-hydroxy esters. Barik, R.; Halder, J; Jana, P. and Nanda, S. Tretrahedron, 2021, 94, Article 132356

tetra image.tif

66. Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction. Chakraborty, J.; Ghosh, A. and Nanda, S. Org. Biomol. Chem, 2020, 18,2331-2345.

untitled.tif

65. Biocatalytic Dynamic Kinetic Reductive Resolution with ketoreductase from Klebsiella pneumoniae: Asymmetric synthesis of functionalized tetrahydropyrans. Barik, R.; Halder, J. and Nanda, S. Org. Biomol. Chem, 2019, 17, 8571-8588.

64. Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic opening of an epoxide. Chakraborty, J. and Nanda, S. Org. Biomol. Chem, 2019, 17, 7369-7379

paper 45.png

63. Asymmetric total synthesis of cryptoconcatone I. Acharyya, R.; Pal, P.; Chatterjee, S and Nanda, S. Org. Biomol. Chem, 2019, 17, 3552-3566.

62. Resorcylic acid lactones (RALs) and their structural congeners: Recent advances in their biosynthesis, chemical synthesis and biology. Jana, N and Nanda, S. New J. Chem. 2018, 42, 17803-17873.

RAL image.png

61. "Asymmetric Total Synthesis of Naturally Occurring Spirocyclic Tetranorsesquiterpenoid Lanceolactone A". Acharyya. R and Nanda, S. Org. Biomol. Chem. 2018, 16, 5027-5035.

60. “Distinctive transformation based diversity oriented synthesis of small ring carbocyles and heterocycles from biocatalytically derived enantiopure α-substituted-β-hydroxyesters ” Halder, J.; Das, D.; Nanda, S. Org. Biomol. Chem. 2018, 16, 2549-2575.

59. Exploration of Ring Rearrangement Metathesis (RRM) Reaction: A General and Flexible Approach for the Rapid Construction of [5,n] fused bicyclic systems en-route to linear triquinanes. Acharyya, R.; Rej, R.; Nanda, S. J. Org. Chem. 2018, 83, 2087-2103.

58. “Asymmetric Synthesis of Ramariolides A and C through Bimetallic Cascade Cyclization and Z–E Isomerization Reaction.” Pal, P.; Nanda, S. Org. Lett, 2017, 19, 1164-1167.

57. “Asymmetric total synthesis of (R)-α-cuparenone, (S)-cuparene and formal synthesis of (R)-β-cuparenone through Meinwald rearrangement and ring closing metathesis (RCM) reaction.” Kumar, R.; Halder, J.; Nanda, S. Tetrahedron, 2017, 73, 809-818.

56. “Asymmetric synthesis of dihydroartemisinic acid through intramolecular stetter reaction”. Rej, R. K.; Acharyya, R. K.; Nanda, S. Tetrahedron, 2016, 72, 4931-4937.

55. “Enantiopure hydroxymethylated cycloalkenols as privileged small molecular multifunctional scaffolds for the asymmetric synthesis of carbocycles”. Kumar, R.; Rej, R. K.; Halder, J.; Mandal. H.; Nanda, S. Tetrahedron: Asymmetry, 2016, 27, 498-512.

54. “Asymmetric total synthesis of paecilomycin F, cochliomycin C, zeaenol, 5-bromo-zeaenol and 3,5-dibromo-zeaenol by Heck coupling and late stage macrolactonization approach”. Pal, P.; Chakraborty, J.; Mali, A.; Nanda, S. Tetrahedron, 2016, 72, 2336-2348.

53. “Enantioselective biocatalytic reduction of 2,2-disubstituted ethylacetoacetates: an indirect desymmetrization approach for the synthesis of enantiopure 4-hydroxy-3,3-disubstitutedpentane-2-ones”. Halder J.; Das, D. Tetrahedron : Asymmetry, 2015, 26, 1197-1208.

52. “Asymmetric total synthesis of (-)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside”. Kumar, R.; Rej, R.; Nanda, S. Tetrahedron : Asymmetry, 2015, 26, 751-759.

51. “Asymmetric synthesis of cytospolides C and D through successful exploration of stereoselective Julia-Kocienski olefination and Suzuki reaction followed by macrolactonization”. Rej, R.; Kumar R.Nanda, S. Tetrahedron, 2015, 71, 3185-3194.

50. “Asymmetric total synthesis of paecilomyci E, 10’-epi-paecilomycin E and 6’-epi-cochliomycin C”. Pal, P. Jana, N.Nanda, S. Org. Biomol. Chem, 2014, 12, 8257-8274.

49. “Stereoselecive synthesis of enantiopure oxetanes, carbohydrate mimic, ε-lactone, and cyclitols from biocatalytically derived β-hydroxyesters as chiral precursors”. Das, D.; Halder J.; Bhuniya, R.Nanda, S. Eur. J. Org. Chem, 2014, 5229-5246.

48. “Asymmetric synthesis of naturally occurring (-)-seimatopolides A and B”. Rej, R.; Pal. P. Nanda, S. Tetrahedron, 2014, 70, 4457-4470.

47. “Asymmetric synthesis of naturally occurring nonenolide xyolide through cross metathesis and macrolactonization reaction”. Rej, R.; Jana, A. Nanda, S. Tetrahedron, 2014, 70, 2634-2642.

46. “Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D,E and their stereoisomers”. Rej, R.Nanda, S. Eur. J. Org. Chem, 2014, 860-871.

45. Chemoenzymatic asymmetric synthesis of fluoxetine, atomoxetine, nisoxetine, and duloxetine”. Rej, R. K.; Das, T.; Hajra, S.; Nanda, S. Tetrahedron: Asymmetry, 2013, 24, 913-918.

44. Asymmetric total synthesis of 5`-epi-cochliomycin C”. Jana, N.; Das, D.; Nanda, S. Tetrahedron, 2013, 69, 2900-2908.

43. “Asymmetric total synthesis of (-)-rasfonin”. Bhuniya, R. Nanda, S. Tetrahedron, 2013, 69, 1153-1165.

42. “Asymmetric total synthesis of 5’-epi-paecilomycin-F”. Jana, N. Nanda, S. Tetrahedron: Asymmetry, 2012, 23, 802-808.

41. “Asymmetric synthesis of cochliomycin-A and zeaenol”. Jana, N. Nanda, S. Eur. J. Org. Chem. 2012, 4313-4320.

40. “Stereoselective synthesis of a novel natural carbasugar and analogues from hydroxymethylated cycloalkenone scaffolds”. Rej, R.; Jana, N.; Kar, S.; Nanda, S. Tetrahedron: Asymmetry, 2012, 23, 364-372.

39. Klebsiella pneumoniae (NBRC 3319) Mediated Asymmetric Reduction of α-Substituted β-Oxo Esters and Its Application to the Enantioiselective Synthesis of Small-Ring Carbocycle Derivatives” Bhuniya, R.; Mahapatra, T.; Nanda, S. Eur. J. Org. Chem, 2012, 1597-1602.

38. “Asymmetric synthesis of both the enantiomers of antidepressant venlafaxine and its analogues”. Bhuniya, R.; Nanda, S. Tetrahedron Letter, 2012, 53, 1990-1992.

37. "Total synthesis of stagonolide-B”. Das, T.; Mahapatra, T.; Nanda, S.; Tetrahedron Letter, 2012, 53, 1186-1189.

36. “Chemoenzymatic total synthesis of stagonolide-E”. Das, T.; Nanda, S. Tetrahedron Letter, 2012, 53, 256-258.

35. “Enantiomeric scaffolding of α-tetralone and related scaffolds by EKR (enzymatic kinetic resolution) and stereoselective ketoreduction with ketoreductases”. Bhuniya, R.; Nanda, S. Org. Biomol. Chem, 2012, 10, 536-547.

34. “Stereoselective desymmetrization of 2,2-bishydroxymethyl-1-tetralones byiodocyclization, synthesis of novel [6,6,5] tricyclic framework and chemo-enzymatic diversity generation”. Mahapatra, T.; Nanda, S. Adv. Syn. Catal, 2011, 353, 2152-2168.

33. “Characterization of a New (R)-hydroxynitrile lyase from the japanese apricot and cDNA cloning and secretory expression of one of the isozymes in Pichia pastoris." Fukuta, Y.; Nanda, S.; Kato, Y.; Yurimoto, H.; Sakai, Y.; Komeda, H.; Asano, Y. Biosci. Biotechnol. Biochem. 2011, 75, 214-220.

32. “Asymmetric synthesis of the active form of loxoprofen and its analogue”.Bhuniya, R.; Nanda, S. Tetrahedron Asymmetry, 2011, 22, 1125-1132.

31. “Asymmetric synthesis of stagonolide-D and stagonolide-G”. Mahapatra, T.; Das, T.; Nanda, S. Bull. Chem. Soc. Jpn, 2011, 84, 511-519.

30. “Asymmetric synthesis of aryl cyclitols based on 1,2,3,4-tetrahydronapthalene scaffolds”. Mahapatra, T.; Nanda, S. Tetrahedron: Asymmetry, 2011, 22, 406- 412.

29. “Asymmetric synthesis of achaetolide”. Das, T.; Bhuniya, R.; Nanda, S. Tetrahedron: Asymmetry, 2010, 21, 2206-2211.

28. “Asymmetric synthesis of hydroxy-skipped bishomoinositols as potential glycosidase inhibitors". Mahapatra, T.; Nanda, S. Tetrahedron: Asymmetry, 2010, 21, 2199-2205.

27. “Asymmetric synthesis of (+)-chloriolide”. Das, T.; Jana, N.; Nanda, S. Tetrahedron Letter, 2010, 51, 2644-2647.

26. “Chemoenzymatic asymmetric synthesis of stagonolide-C”. Jana, N.; Mahapatra, T.; Nanda, S. Tetrahedron Asymmetry, 2009, 20, 2622-2628.

25. Chemoenzymatic asymmetric total synthesis of Penienone”. Mahapatra T.; Bhunya, R.Nanda, S. Tetrahedron Lett, 2009, 50, 5392-5394.

24. "Prunus armeniaca hydroxynitrile lyase (ParsHNL) catalyzed asymmetric synthesis of cyanohydrins from sterically demanding aromatic aldehydes”. Bhunya, R.; Mahapatra, T.; Nanda, S. Tetrahedron: Asymmetry, 2009, 20, 1526-1530.

23. “Prunus armeniaca hydroxynitrile lyase (ParsHNL) catalyzed synthesis of δ, ε-unsaturated cyanohydrins”. Bhunya, R.; Jana, N.; Das, T.; Nanda, S. Synlett, 2009, 1237-1240.

22. “Asymmetric synthesis of (+)-Palitantin by an enzymatic and organocatalytic approach”. Mahapatra, T.; Nanda, S. Tetrahedron: Asymmetry, 2009, 20, 610-615.

21. “Enantioselective enzymatic desymmetrization of prochiral 1,3-diols and enzymatic resolution of monoprotected 1,3-diols based on α-tetralone and related multifunctional scaffolds” Mahapatra, T.; Das, T.; Nanda, S. Tetrahedron: Asymmetry, 2008, 19, 2497-2507.

20. “Chemoenzymatic synthesis and resolution of compounds containing a quaternary stereocenters adjacent to carbonyl groups”. Mahapatra, T.; Jana, N.; Nanda, S. Tetrahedron: Asymmetry, 2008, 19, 1224-1232.

Publications from PhD and post-doctoral work

19. “Characterization of a New (R)-hydroxynitrile lyase from the japanese apricot Prunus mume and cDNA cloning and secretory expression of one of the isozymes in Pichia pastoris. Fukuta, Y.; Nanda, S.; Kato, Y.; Yurimoto, H.; Sakai, Y.; Komeda, H.; Asano, Y. Biosci. Biotechnol. Biochem. 2011, 75, 214-220.

18. “Studies on taxadiene synthase: interception of the cyclization cascade at the verticillene stage and rearrangement to phomactatriene”. Chow, S. Y.; Williams, H. J.; Penington, J. D.; Nanda, S.; Reibenspies, J. H.; Scott, A. I. Tetrahedron, 2007, 63, 6204-6209.

17. “PmHNL catalyzed synthesis of (R)-cyanohydrins derived from aliphatic aldehydes” Nanda, S., Kato, Y., Asano, Y. Tetrahedron:Asymmetry, 2006, 17, 735-741.

16. “A new (R)-mandelonitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins”. Nanda, S., Kato, Y., Asano, Y. Tetrahedron, 2005, 61, 10908-10916.

15. “Studies on Taxadiene synthase: Interception of the cyclization cascade at the isocembrene stage With GGPP analogues”. Chow, S. Y.; Williams, H.J.; Huang, Q.; Nanda, S.; Scott, A. I. J. Org. Chem, 2005, 70, 9997-10003.

14. “Chemoenzymatic total synthesis of the phytotoxic lactone Herbarumin III” Nanda, S. Tetrahedron Letters, 2005, 46, 3661-63.

13. “A Highly Efficient Chemoselective Synthesis of 3, 5-diketoesters by Lipase Catalyzed Transesterification: Application to the resolution of secondary alcohols. Nanda, S., Scott, A. I. Journal of Molecular Catalysis, B (Enzymatic). 2004, 30, 1-12.

12. “Asymmetric Synthesis of (E) and (Z) 3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid”. Nanda, S., Scott, A. I. Tetrahedron: Asymmetry, 2004, 15, 963-970.

11. “Lipoxygenase Biocatalysis: A survey of asymmetric oxygenation”.Nanda, S., Yadav, J. S. Journal of Molecular Catalysis B: Enzymatic. 2003, 26, 3-28.

10. “Asymmetric Synthesis of Unnatural (Z, Z, E) Octadecatrienoid and Eicosatrienoid by Lipoxygenase Catalyzed Oxygenation”. Nanda, S. Yadav, J. S. Tetrahedron : Asymmetry. 2003, 14, 1799-1806.

9. “An efficient enantioselective reduction of ketones with Daucus Carota root”.Yadav, J.S.; Nanda, S.; Reddy, P. T.; Bhaskar Rao, A. J. Org. Chem. 2002, 67, 3900-3903.

8. “Design and synthesis of useful intermediates for novel lipoxygenase substrates through enzymatic resolution”. Yadav, J. S.; Nanda, S.; Bhaskar Rao, A. Tetrahedron: Asymmetry, 2001, 12, 53- 57.

7. “Soybean Lipoxygenase and Horseradish peroxidase Catalyzed Asymmetric Oxidation Reduction Sequence for the Synthesis of Chiral (Z, E) diene-diol”. Yadav, J. S.; Nanda, S.; Bhaskar Rao, A. Synlett. 2001, 787-788.

6. “Enzymatic Asymmetric Hydroxylation of Unnatural Substrates with Soybean Lipoxygenase”. Yadav, J. S.; Nanda, S.; Bhaskar Rao, A. Tetrahedron: Asymmetry, 2001, 12, 2129-2135.

5. “A Facile Synthesis of (R)-(-)-2-azido-1-arylethanols from 2-azido-1-arylketones Using Baker’s Yeast”. Yadav, J. S.; Reddy, P. T.; Nanda, S.; Bhaskar Rao, A. Tetrahedron: Asymmetry, 2001, 12, 63-67.

4. “Bromosulfonamidation of Alkenes using S, S-dimethyl-N-(p-toluenesulfonyl) sulfilimine”.Raghavan, S.; Reddy, S. R.; Tony, K. A.; Naveen Kumar, Ch.; Nanda, S. Synlett, 2001, 851-853.

3. “Novel Chiral lipoxygenase substrates: Design and Synthesis Part II”. Yadav, J. S.; Nanda, S.; Bhaskar Rao, A. Tetrahedron: Asymmetry. 2001, 12, 3223-3234.

2. “Stereoselective synthesis of (R)-Denopamine, (R)-Tembamide and (R)-Aegeline via asymmetric reduction of azidoketones by Daucus carota in aqueous medium”. Yadav, J. S.; Reddy, P. T.; Nanda, S.; Bhaskar Rao, A. Tetrahedron: Asymmetry. 2001, 12, 3381-3385.

1. “Enzyme Catalyzed Kinetic Resolution of Racemic 2, 2-dimethyl-3-(2, 2-disubstituted vinyl) Cyclopropane Carboxylic Acids Anchored on Polymer supports”. Nanda, S.; Bhaskar Rao, A.; Yadav, J. S. Tetrahedron Letters, 1999, 40, 5905-5908.

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