Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement
| Autor: | Takaaki Sato, Yuichiro Maeda, Noritaka Chida, Naoto Hama, Yasuaki Nakayama |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
inorganic chemicals
Allylic rearrangement 010405 organic chemistry Stereochemistry Chemistry organic chemicals Organic Chemistry Enantioselective synthesis food and beverages Total synthesis Sigmatropic reaction 010402 general chemistry 01 natural sciences Catalysis Carroll rearrangement 0104 chemical sciences Claisen rearrangement Enantiopure drug polycyclic compounds heterocyclic compounds Chirality (chemistry) |
| Zdroj: | Synthesis. 48:1647-1654 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0035-1561948 |
| Popis: | The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process. |
| Databáze: | OpenAIRE |
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