Symmetry Breaking Routes to Natural and Unnatural Ladderanes

Portrait of Prof. Santanu Mukherjee, guest speaker
Date & Time:
-
Location:
iSTEM Building 2, Room 1218

Breaking symmetry to generate asymmetry, commonly termed desymmetrization, is a remarkably powerful strategy for building molecular complexity. Successful implementation of this strategy holds the potential to forge multiple stereogenic centers in a single step. In fact, stereocenters can also be created away from the reaction site. 

During the past few years, we have developed a number of organocatalytic enantioselective desymmetrization reactions including formal C(sp2)‒H alkylation1 and de novo construction of (hetero)arenes. 2 We subsequently applied these reactions to the enantioselective synthesis complex targets. 

Naturally occurring ladderane phospholipids represent a class of targets, which provided us with the motivation to develop some of these enantioselective desymmetrization reactions. This talk will focus on the application of our desymmetrizing C(sp2)‒H alkylation reaction to [3]- ladderanol, 3 [5]-ladderanoic4 acid as well as their unnatural analogues in an effort to unravel their biosynthetic hypothesis. In addition, our recent work on the enantioselective synthesis of an unnatural benzo-analogue of [3]-ladderanol through the application of our newly developed alkoxy-directed dienamine catalysis5 will also be discussed.

Desymmetrizing reactions in ladderanol and ladderanoic acid

References: 

  1. (a) Manna, M. S.; Mukherjee, S. J. Am. Chem. Soc. 2015, 137, 130. (b) Sarkar, R.; Mukherjee, S. Org. Lett. 2016, 18, 6160. (c) Mallojjala, S. C.; Sarkar, R.; Karugu, R. W.; Manna, M. S.; Ray, S.; Mukherjee, S.; Hirschi, J. S. J. Am. Chem. Soc. 2022, 144, 17399.
  2. (a) Ghosh, B.; Harariya, M. S.; Mukherjee, S. Angew. Chem. Int. Ed. 2022, 61, e202204523. (b) Ghosh, B.; Balhara, R.; Jindal, G.; Mukherjee, S. Angew. Chem. Int. Ed. 2021, 60, 9086.
  3. Ray, S.; Mondal, S.; Mukherjee, S. Angew. Chem. Int. Ed. 2022, 61, e202201584.
  4. Ray, S.; Das, S.; Behera, D.; Biswas, P.; Tarafdar, P. K.; Mukherjee, S. ChemRxiv, 2025, DOI: 10.26434/chemrxiv-2025-gmdmv
  5. Ray, S.; Behera, D.; Harariya, M. S.; Das, S.; Tarafdar, P. K.; Mukherjee, S. J. Am. Chem. Soc. 2025, 147, 2523.
Type of Event:
Organic Seminar
Research Areas:
Organic Chemistry
Prof. Santanu Mukherjee
Department:
Department of Organic Chemistry
Indian Institute of Science, Bangalore
Learn more about Prof. Mukherjee and his research https://orgchem.iisc.ac.in/santanu_mukherjee/SM.htm