Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid
| Autor: | Erin L. Kuker, M. Kevin Brown, Erin N. Hancock, Dean J. Tantillo |
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| Rok vydání: | 2020 |
| Předmět: |
Biological Products
Strain (chemistry) Chemistry Stereochemistry natural products Organic Chemistry Enantioselective synthesis Carboxylic Acids Stereoisomerism General Chemistry General Medicine Article Catalysis Cycloaddition Cyclobutane chemistry.chemical_compound reaction mechanisms Drug Stability copper strained molecules Chemical Sciences Cyclobutanes cycloaddition |
| Zdroj: | Angewandte Chemie (International ed. in English), vol 59, iss 1 Angew Chem Int Ed Engl |
| Popis: | The synthesis of structurally complex and highly strained natural products provides unique challenges and unexpected opportunities for the development of new reactions and strategies. Herein, the synthesis of (+)-[5]-ladderanoic acid is reported. En route to the target, unusual and unexpected strain release driven transformations were uncovered. This occurrence required a drastic revision of the synthetic design that ultimately led to the development of a novel stepwise cyclobutane assembly by an allylboration/Zweifel olefination sequence. |
| Databáze: | OpenAIRE |
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