Total synthesis of (+)-13-deoxytedanolide.
A total synthesis of 13-deoxytedanolide is described. The synthesis features a highly stereoselective fragment assembly aldol reaction of methyl ketone 4 and aldehyde 5 to establish the complete carbon skeleton of the natural product in the form of aldol 15. The facile formation of the remarkably unreactive hemiketal 16 thwarted attempts to elaborate 15 to tedanolide. However, deoxygenation of the C(13)-hydroxyl of 16 provided the 13-deoxy hemiketal 17 that was smoothly elaborated to 13-deoxytedanolide.
Julian
Lisa D
LD
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Newcom
Jason S
JS
Roush
William R
WR
D000818:Animals; D018942:Macrolides / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
C409106:13-deoxytedanolide; D018942:Macrolides