Stereodivergent Attached‐Ring Synthesis via Non‐Covalent Interactions: A Short Formal Synthesis of Merrilactone A
| Autor: | Benjamin J. Huffman, Yusuke Hanaki, Tiffany Chu, Jonathan L. Wong, Ryan A. Shenvi, K. N. Houk, Shuming Chen |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
natural products
Stereochemistry Ring (chemistry) Article Catalysis Lactones chemistry.chemical_compound Formal synthesis Michael addition synthesis design Non-covalent interactions chemistry.chemical_classification attached-ring Molecular Structure Chemistry Organic Chemistry Diastereomer Stereoisomerism General Chemistry General Medicine Bond formation diastereoselectivity Merrilactone A Cyclization Chemical Sciences Michael reaction Selectivity Sesquiterpenes |
| Zdroj: | Angewandte Chemie (International ed. in English), vol 61, iss 3 Angew Chem Int Ed Engl |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.202114514 |
| Popis: | A strategy to control the diastereoselectivity of bond formation at a prochiral attached-ring bridgehead is reported. An unusual stereodivergent Michael reaction relies on basic vs. Lewis acidic conditions and non-covalent interactions to control re- vs. si- facial selectivity en route to fully substituted attached-rings. This divergency reflects differential engagement of one rotational isomer of the attached-ring system. The successful synthesis of an erythro subtarget diastereomer ultimately leads to a short formal synthesis of merrilactone A. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text