Total Synthesis of (+)-Dixiamycin C via a Late-Stage Ni(II)-Photoredox <i>N</i>-Arylation of Carbazoles
We report the asymmetric total synthesis of dixiamycin C (1) through the shrewd alliance of the naturally occurring monomer xiamycin A methyl ester (5) and its bromo derivative (31) following a late-stage Buchwald-Macmillan's C-N bond formation via a photoredox electron transfer approach with a less reactive carbazole nitrogen. The key step in the synthesis of monomer xiamycin A methyl ester (5) involves Buchwald's Pd(II)-mediated aerobic dehydrogenative C-N bond formation, Beckmann rearrangement, and <i>ipso</i>-acetylation of an electron-rich aromatic ring of an abietane core.
Authors
- Alakesh Bisai (ORCID: https://orcid.org/0000-0001-5295-9756)
- Arindam Khatua (ORCID: https://orcid.org/0000-0001-5847-5090)
- Sovan Niyogi (ORCID: https://orcid.org/0000-0001-5501-4088)
- Monosij Nandy (ORCID: https://orcid.org/0000-0002-9685-1322)
- Ayan Mondal (ORCID: https://orcid.org/0000-0002-1617-3921)
- Souvik Pal
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
- Indian Institute of Science Education and Research, Bhopal (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-21
- DOI
- https://doi.org/10.1021/acs.orglett.4c02436
- Citations
- 5
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India
- Ministry of Education, India
- Science and Engineering Research Board