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Natural Product Chemistry Lab
Department of Applied Chemistry Faculty of Engineering, Osaka Institute of Technology
Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of communiol E
![Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of communiol E](https://static.wixstatic.com/media/4b21d2_a2031dac253e47fb90aa979e6d1299d6~mv2.jpeg/v1/fill/w_680,h_657,al_c,q_85,usm_0.66_1.00_0.01,enc_auto/JOC2021_edited.jpeg)
A convenient, stereocontrolled route to branched cis-fused bicyclic ethers through halolactonization, α-bromination, and oxy-Favorskii rearrangement is developed. The total synthesis of communiol E, a bicyclic polyketide isolated from Podospora communis, was achieved based on this method.
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