Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti-Carbopalladation/Heck Cascade as the Key Step
| Autor: | Daniel B. Werz, Peter G. Jones, Martin Pawliczek, Bastian Milde |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound Stereospecificity Lysergol chemistry Cascade reaction Cascade Heck reaction Yield (chemistry) Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 19:1914-1917 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The enantioselective synthesis of (+)-lysergol was completed in 12 steps and an overall yield of 13% starting from a known literature precursor. The key step relies on a domino reaction containing a formal anti-carbopalladation, which is terminated by a β-silyl-directed Heck reaction. During this transformation, the two six-membered rings of the ergot scaffold are formed in a completely stereospecific manner. |
| Databáze: | OpenAIRE |
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