A short access to 3-hydroxy-4-hydroxymethyltetrahydrofurans: application to the total synthesis of amphiasterin B4.
The first total synthesis of amphiasterin B4, a secondary metabolite previously isolated from Plakortis quasiamphiaster has been achieved. The core structure has been reached according to a highly stereoselective one-pot epoxidation/cyclization of an unsaturated diol. This substrate can be prepared from beta,gamma-unsaturated diesters readily available from the organocatalyzed protonation of a transient dienol generated by UV irradiation of corresponding alpha,beta-unsaturated isomers.
Salim
Hani
H
Université de Lyon, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire, 43 Boulevard du 11 novembre 1918, 69622 Villeurbanne Cedex, France.
Piva
Olivier
O
D000818:Animals; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D047229:Plakortis / Q000737:chemistry*; D013045:Species Specificity; D013237:Stereoisomerism
D005663:Furans; C551688:amphiasterin B4