Catalytic Asymmetric Approach to the Naturally Occurring Clavine Alkaloid (+)-Lysergine
Abstract An efficient asymmetric approach to the ergot alkaloids has been achieved via a highly regioselective Heck cyclization. Asymmetric induction of the key intermediate was achieved via a catalytic enantioselective α-aminoxylation catalyzed by d-proline (98% ee). Utilizing the aforementioned strategy, formal total synthesis of the ergot alkaloids (+)-lysergine and (+)-isolysergine has been achieved. Importantly, an asymmetric approach to the unnatural analogues (–)-lysergine and (–)-isolysergine has also been achieved via catalytic enantioselective α-aminoxylation using l-proline.
Authors
- Mrinal K. Das (ORCID: https://orcid.org/0000-0003-2030-299X)
- Kundan Shaw (ORCID: https://orcid.org/0000-0003-1532-9055)
- Debabrata Mondal (ORCID: https://orcid.org/0009-0007-8834-7525)
- Saikat Chaudhuri (ORCID: https://orcid.org/0009-0005-5927-932X)
- Alakesh Bisai (ORCID: https://orcid.org/0000-0001-5295-9756)
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
- Indian Institute of Science Education and Research, Bhopal (IN)
- University of Kalyani (IN)
Publication Details
- Journal
- Synthesis
- Published
- 2024-08-13
- DOI
- https://doi.org/10.1055/a-2385-5110
- Citations
- 1
- Primary Topic
- Plant and fungal interactions
- Type
- article
- Field-Weighted Citation Impact
- 1.03
Funders
- Council of Scientific and Industrial Research, India
- Ministry of Education, India
- Indian Institute of Science Education and Research Bhopal
- Science and Engineering Research Board