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A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A.

ABSTRACT: A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional groups are tolerated and the synthetic utility of this method has been demonstrated through a series of transformations of the allene moiety. By applying this reaction as the key step, the total syntheses of naturally occurring allenic aromatic ethers, eucalyptene and terricollene A (first synthesis; 4.5 g gram scale), have been accomplished.

SUBMITTER: Huang C

PROVIDER: S-EPMC8278932 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A.

Huang Chaofan C Shi Fuchun F Cui Yifan Y Li Can C Lin Jie J Liu Qi Q Qin Anni A Wang Huanan H Wu Guolin G Wu Penglin P Xiao Junzhe J Xu Haibo H Yuan Yuan Y Zhai Yizhan Y Zheng Wei-Feng WF Zheng Yangguangyan Y Yu Biao B Ma Shengming S

Chemical science 20210609 27

A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional groups are tolerated and the synthetic utility of this method has been demonstrated through a series of transformations of the allene moiety. By applying this reaction as the key step, the total syntheses of naturally occurring allenic aromatic ...[more]

PMID: 34349905

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