Asymmetric Formal Total Syntheses of (+)- and (−)-Limaspermidine from Chirally Resolved 2-Pyrone Diels–Alder Cycloadducts via Aromatic C–H Amidation and Imino-Diels–Alder Reaction
A new asymmetric synthetic route to (+)- and (-)-limaspermidine was devised, starting with chirally resolved enantiomerically pure 2-pyrone Diels-Alder cycloadducts. This route utilizes intramolecular Pd-catalyzed aromatic C-H amidation and imino-Diels-Alder reactions to construct the key indoline and indolizidine subunits onto the central cyclohexane core, allowing the straightforward formal total syntheses of both (+)- and (-)-limaspermidine.
Authors
- Vitaly Kovalenko (ORCID: https://orcid.org/0000-0003-3426-2300)
- Sang‐Ha Oh
- Quoc Anh Ngo (ORCID: https://orcid.org/0000-0002-2319-2880)
- Cheon‐Gyu Cho (ORCID: https://orcid.org/0000-0003-4851-5671)
- Ngoc Binh Vo (ORCID: https://orcid.org/0009-0009-6973-8402)
- Joo-Yeon Oh
Institutions
- Belarussian State Pedagogical University Named After Maxim Tank (BY)
- Hanyang University (KR)
- Vietnam Academy of Science and Technology (VN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-31
- DOI
- https://doi.org/10.1021/acs.joc.4c01696
- Citations
- 2
- Primary Topic
- Alkaloids: synthesis and pharmacology
- Type
- article
- Field-Weighted Citation Impact
- 0.93
Funders
- Belarusian Republican Foundation for Fundamental Research
- Vietnam Academy of Science and Technology
- National Research Foundation of Korea