Asymmetric total syntheses of immunosuppressive diterpenoids triptobenzenes N and R <i>via</i> a remote Csp<sup>3</sup>–H functionalization
The total syntheses of the naturally occurring diterpenoids triptobenzenes N (1c) and R (1d) have been accomplished <i>via</i> a late-stage δ-Csp<sup>3</sup>-H functionalization of an enone intermediate. The highly functionalized dienone intermediate 2 was utilized as a common scaffold for this study. An XRD analysis of compounds 8 and 4 confirmed the stereochemistry of the quaternary centers of the abietane core. Finally, a chemoselective ketal protection and reduction completed the first total syntheses of the immunosuppressive diterpenoids triptobenzenes N (1c) and R (1d).
Authors
- Mintu Munda (ORCID: https://orcid.org/0000-0003-3414-8305)
- Nanda Kishore Roy (ORCID: https://orcid.org/0009-0009-9637-4464)
- Alakesh Bisai (ORCID: https://orcid.org/0000-0001-5295-9756)
- Sovan Niyogi (ORCID: https://orcid.org/0000-0001-5501-4088)
- Ranjit Murmu (ORCID: https://orcid.org/0000-0002-2244-5647)
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
- Indian Institute of Science Education and Research, Bhopal (IN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc02354h
- Citations
- 1
- Primary Topic
- Biological Activity of Diterpenoids and Biflavonoids
- Type
- article
- Field-Weighted Citation Impact
- 0.81
Funders
- Council of Scientific and Industrial Research, India
- Science and Engineering Research Board