Development of diastereoselective birch reduction-alkylation reactions of bi- and tricyclic beta-alkoxy-alpha,beta-unsaturated ketones.
Diastereoselective Birch reduction-alkylation reactions of bicyclic beta-alkoxy-alpha,beta-unsaturated carbonyl compounds and tricyclic analogues were investigated. Although the relative configuration of the product was altered according to the structure of the starting material, stereoselectivity of the reaction could be accounted for by similar reaction pathways. The product from the tricyclic beta-alkoxy-alpha,beta-unsaturated carbonyl compound corresponded to the trichothecene skeleton.
Hiroya
Kou
K
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aramaki, Aza Aoba, Aoba-ku, Sendai 980-8578 Japan. hiroya@mail.tains.tohoku.ac.jp
Ichihashi
Yusuke
Y
Furutono
Ai
A
Inamoto
Kiyofumi
K
Sakamoto
Takao
T
Doi
Takayuki
T
D000478:Alkylation; D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D007659:Ketones; D002244:Carbon