Biomimetic syntheses of myrtucommulones K-L and N, and callistiviminenes F-H

[Display omitted] A concise and collective biomimetic synthesis of myrtucommulones K-L and N, as well as callistiviminenes F-H, has been achieved utilizing a mild Me2AlCl-mediated hetero-Diels-Alder reaction as a pivotal step, all in only three steps without the need for protecting groups from readi...

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Bibliographic Details
Published in:Tetrahedron letters 2024-06, Vol.142, p.155080, Article 155080
Main Authors: Zhang, Tian-Hong, Chen, Bo-Yong, Qi, Ming-Fang, Zhao, Fen, Lin, Shi-Lin, Ye, Wen-Cai, Cheng, Min-Jing, Zhang, Yong-Wen, Wang, Lei
Format: Article
Language:English
Subjects:
Biomimetic synthesis
Callistiviminene
Hetero-Diels-Alder reaction
Me2AlCl
Myrtucommulone
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Summary:[Display omitted] A concise and collective biomimetic synthesis of myrtucommulones K-L and N, as well as callistiviminenes F-H, has been achieved utilizing a mild Me2AlCl-mediated hetero-Diels-Alder reaction as a pivotal step, all in only three steps without the need for protecting groups from readily available compounds. This approach exhibits excellent regioselectivity and good diastereoselectivity, operates under exceptionally mild conditions, and delivers good yields. Furthermore, this synthesis has led to the revision of the structure of myrtucommulone L.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2024.155080