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Asymmetric Formal Total Syntheses of (+)- and (-)-Limaspermidine from Chirally Resolved 2-Pyrone Diels-Alder Cycloadducts via Aromatic C-H Amidation and Imino-Diels-Alder ReactionAsymmetric Formal Total Syntheses of (+)- and (−)-Limaspermidine from Chirally Resolved 2-Pyrone Diels-Alder Cycloadducts via Aromatic C-H Amidation and Imino-Diels-Alder Reaction
- Other Titles
- 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
- Issue Date
- Sep-2024
- Publisher
- American Chemical Society
- Citation
- The Journal of Organic Chemistry, v.89, no.18, pp 13501 - 13510
- Pages
- 10
- Indexed
- SCIE
SCOPUS
- Journal Title
- The Journal of Organic Chemistry
- Volume
- 89
- Number
- 18
- Start Page
- 13501
- End Page
- 13510
- ISSN
- 0022-3263
1520-6904
- Abstract
- 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.
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Related Researcher
- Cho, Cheon Gyu
- COLLEGE OF NATURAL SCIENCES (DEPARTMENT OF CHEMISTRY)