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  • Title: Total synthesis of (+)-13-deoxytedanolide.
    Author: Julian LD, Newcom JS, Roush WR.
    Journal: J Am Chem Soc; 2005 May 04; 127(17):6186-7. PubMed ID: 15853320.
    Abstract:
    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.
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