A concise total synthesis of the lichen macrolide (+)-aspicilin.
The total synthesis of the polyhydroxylated macrolide (+)-aspicilin 5 is described using as a key step a highly diastereoselective allylation of aldehyde 6 with the uniquely functionalized allylstannane 1. (+)-Aspicilin is obtained in 18 steps and 10% overall yield. [structure: see text]
Dubost
Christophe
C
Université Catholique de Louvain, Département de Chimie, 1 Place Louis Pasteur, B-1348 Louvain La Neuve, Belgium.
Markó
Istvan E
IE
Ryckmans
Thomas
T
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008011:Lichens / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; D018942:Macrolides; C418323:aspicilin