Journal of the American Chemical Society

Total synthesis of elisabethin A: Intramolecular Diels-Alder reaction under biomimetic conditions

TJ Heckrodt, J Mulzer

文献索引：Heckrodt, Thilo J.; Mulzer, Johann Journal of the American Chemical Society, 2003 , vol. 125, # 16 p. 4680 - 4681

全文：HTML全文

被引用次数: 63

摘要

We describe the first total synthesis of the marine diterpenoid elisabethin A. The synthesis uses (S)-hydroxy-2-methyl-propionate as the chiral starting material, which is elaborated into a dienyl-iodide and added to an aryl acetic acid ester via enolate alkylation. The hydroquinoid system is oxidized to the quinone which serves as the dienophile in a highly stereocontrolled intramolecular Diels-Alder addition. This IMDA reaction, which to our ...