Department of Chemistry Colloquium on “Biomimetic Total Synthesis of Biologically Relevance Natural Products”

Nature produces a variety of complex natural products in entioenriched form (see, Figure).1-2 Since these are isolated from Nature in limited quantity (mostly in mg scale), total synthesis endeavors play a crucial role in bioactivity evaluation by providing access to significant quantity.3 This also provides platform for the invention of oxidative strategies for chemical synthesis, such as C-C, C-N, and N-N bond forming reactions.4-5 Since these processes avoid a protection and deprotection groups, the development of methodologies following aerobic oxidations are welcome to synthesize value added organic molecules, particularly for the synthesis of natural products and in pharmaceutical industries.

In the above context, naturally occurring alkaloids with impressive diversity of biological activities drew our interest for the development of strategies to form C-C, C-N, and N-N bonds under oxidative conditions.1a Interestingly, a variety of alkaloids of this family show interesting biological activities, such as antibacterial and cytotoxic activities.1a Towards this direction, we explored novel oxidative strategies under mild condition that will be discussed in this talk.6

References & Notes:

  1. (a) Overman et. al. J. Am. Chem. Soc. 2001, 123, 9465. (b) Nicolaou et. al. Angew. Chem., Int. Ed. 2001, 40, 2482. (c) Movassaghi et. al. Angew. Chem., Int. Ed. 2008, 47, 1485. (d) Baran et. al. J. Am. Chem. Soc. 2014, 136, 5571. (e) Sarpong et. al. Angew. Chem., Int. Ed. 2019, 58, 15304. (f) Hertweck et. al. Angew. Chem., Int. Ed. 2013, 125, 9210.
  2. (a) N. Kumar, M. K. Das, S. Ghosh, A. Bisai, Chem. Commun. 2017, 53, 2170. (a) N. Babu, A. Roy, M. Singh, A. Bisai, Org. Lett. 2018, 20, 6327. (b) M. K. Das, N. Kumar, A. Bisai, Org. Lett. 2018, 20, 4421.
  3. (b) S. Bhunia, S. Chaudhuri, A. Bisai, Chem. -Eur. J. 2017, 23, 11234. (c) N. Babu, L. K. Kinthada, P. P. Das, A. Bisai, Chem. Commun. 2018, 54, 7963. (d) S. Sharma, A. Roy, K. Shaw, A. Bisai, A. Paul J. Org. Chem. 2020, 54, 14926.
  4. (a) A. Roy, M. K. Das, S. Chaudhuri, A. Bisai, Chem. Commun. 2018, 54, 940. (b) S. Chaudhuri, S. Bhunia, A. Roy, M. K. Das, A. Bisai, Org. Lett. 2018, 20, 288. (c) N. Kumar, A. Maity, V. R. Gavit, A. Bisai, Chem. Commun. 2018, 54, 9083.
  5. (a) K. Shaw, S. Sharma, A. Khatua, A. Paul, A. Bisai, Org. Biomol. Chem. 2021, 19, 9390. (b) A. Khatua, P. Shyamal, S. Pal, A. Mondal, A. Bisai, Chem. Commun. 2022, 58, 3929. (b) S. Sharma, S. Shaheeda, K. Shaw, A. Bisai, and A. Paul, ACS Catal. 2023, 13, 2118.
  6. (a) M. Munda, R. Nandi, S. Kundu, V. R. Gavit, S. Niyogi, A. Bisai Chem. Sci. 2022, 13, 11666. (b) R. Nandi, S. Niyogi, S. Kundu, V. R. Gavit, M. Munda, A. Bisai Chem. Sci. 2023, 14, 8047.

Bio-sketch: Alakesh obtained his Ph.D. from IIT Kanpur in Sept. 2006 working with Prof. Vinod K. Singh. Immediately afterward, he moved to the University of California, Berkeley, CA, where he held a postdoctoral position with Prof. Richmond Sarpong (Sept. 2006 – Dec. 2009). During his stay at Berkeley, he completed the total synthesis of ‘lycopodium alkaloids’ lyconadin A, that received considerable attention from the synthetic community. In Dec. 2009, he left Berkeley and joined Department of Chemistry, IISER Bhopal as an Assistant Professor of Chemistry, later he was promoted to Associate Professor followed by Professor (Jan., 2018) and continued his Academic journey till May, 2020. Meanwhile, he moved to the Department of Chemical Sciences, IISER Kolkata in May, 2019.

The research focus of the AB research group includes the total synthesis of architecturally interesting and biologically active natural products that provide an ideal platform for the invention of new strategies and highly selective organic transformations. His total synthesis has been highlighted twice in ‘Organic Chemistry Portal’ as ‘The Bisai Synthesis of (-)-Physovenine’ (2018) and ‘The Bisai Synthesis of Lycoramine’ (2023).

The research of the AB Group has been appreciated in various forms, to name a few notable ones:

  1. Srikrishna Memorial Lecture (2023, UoH); CDRI Award (2022, CSIR-CDRI) (Excellence in Drug Research); ‘Special Call’ on ‘Reagentless Chemistry’ (2022, SERB); Silver Medal, Chirantan Rasayan Sanstha (2021, VU); D. Nasipuri Memorial Lecture Award (2021, ICS); Bronze Medal, Chemical Research Society of India (2021); Fellow, Indian Chemical Society (FICS-2020); SERB-STAR Award (STAR-2020); CRSI Young Scientist Award (2018); DST Young Scientist Research Grant (2013); BRNS Young Scientist Award & Grant (2011); GRC Award to Postdoc. by Chair, 17th GRC (2008); Postdoc. Fellowship, UC Berkeley (2006-2009)