| Autor: |
Jung ME; Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu, Zhang TH, Lui RM, Gutierrez O, Houk KN |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2010 Oct 15; Vol. 75 (20), pp. 6933-40. |
| DOI: |
10.1021/jo101533h |
| Abstrakt: |
While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13, heating the corresponding ether 18 to 110 °C for 4 h afforded a quantitative yield of the desired cycloadduct 19, which could be easily reduced to the perhydrophenanthrene, an ABC ring analogue of fusidic acid 1. Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
|
