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  • Title: Scalable asymmetric total syntheses of (+)-Psoracorylifol B and (+)-ent-Psoracorylifol C.
    Author: Ren J, Liu Y, Song L, Tong R.
    Journal: Org Lett; 2014 Jun 06; 16(11):2986-9. PubMed ID: 24819702.
    Abstract:
    The first, asymmetric total syntheses of potent antimicrobial Psoracorylifol B (>1.3 g obtained, dr 10.5:1) with a 9.4% overall yield on a gram scale in 14 steps and ent-Psoracorylifol C with a 4.3% yield in 16 steps were achieved. The key features of our synthesis include (i) sequential, rarely explored Achmatowicz rearrangement/bicycloketalization to construct the 6,8-dioxabicyclo[3.2.1]octane core, and (ii) Cu-mediated SN2' methylation or Johnson-Claisen rearrangement to stereoselectively install the all-carbon quaternary stereocenter. This concise, highly efficient, and scalable synthetic route may provide expedited and practical access to psoracorylifols and their analogues for further biological activity evaluation.
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