Total Synthesis of Viridiofungins A and B
| Autor: | Jonathan M. White, Mark A. Rizzacasa, Liselle Atkin, Angus Robertson |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Cyclobutene Bicyclic molecule 010405 organic chemistry Alkene Stereochemistry Organic Chemistry Total synthesis 010402 general chemistry Metathesis 01 natural sciences Biochemistry 3. Good health 0104 chemical sciences chemistry.chemical_compound chemistry Amide Physical and Theoretical Chemistry Isomerization Lactone |
| Zdroj: | Organic Letters. 23:3557-3560 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c00971 |
| Popis: | The total synthesis of viridiofungins A (1) and B (2) via β-lactone 3 in 13 steps is reported. Key steps included an HF-mediated rearrangement of cyclobutene diester 9 to form a bicyclic lactone 6, an olefin cross metathesis between disubstituted alkene 3 and alkene 4 in which isomerization was suppressed, and a novel β-lactone ring opening to form the amide. Deprotection then gave either viridiofungin A (1) or B (2) in high yield. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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