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Natural Product Chemistry Lab
Department of Applied Chemistry Faculty of Engineering, Osaka Institute of Technology
Stereocontrolled Total Synthesis of (+)-Isolaurenidificin and (−)-Bromlaurenidificin
![Stereocontrolled Total Synthesis of (+)-Isolaurenidificin and (−)-Bromlaurenidificin](https://static.wixstatic.com/media/4b21d2_f903173517604ecc9d87e21c572a85fb~mv2.jpeg/v1/fill/w_680,h_657,al_c,q_85,usm_0.66_1.00_0.01,enc_auto/JOC2021_edited.jpeg)
The first total syntheses of (+)-isolaurenidificin and (−)-bromlaurenidificin, the latest acetogenins of the 2,6-dioxabicyclo[3.3.0]octane class, were reported. The synthesis features a completely stereoselective one-pot epimerization-ring contraction to establish the cis configuration with respect to C10-H and C12-H of the tetrahydrofuran ring. Six stereogenic centers and an olefin geometry were constructed in a highly stereoselective manner. Absolute configurations of the natural products were deduced by the comparison of NMR data and specific rotations.
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