Concise synthesis of moracin M using Appel mediated dehydration of a bioinspired endoperoxide

[Display omitted] A synthesis of moracin M using Appel dehydration of a biomimetic inspired endoperoxide and subsequent late stage aromatization, is described. A key 1,3-diene, obtained from a base-free Suzuki-Miyaura coupling, can undergo biomimetic oxidation to its endoperoxide, followed by dehydr...

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Bibliographic Details
Published in:Tetrahedron letters 2023-01, Vol.114, p.154273, Article 154273
Main Authors: Al-Jawaheri, Yassir, Elsegood, Mark R.J., Mistry, Jai-Ram, Kimber, Marc C.
Format: Article
Language:English
Subjects:
Benzofuran
Biomimetic
Endoperoxide
Moracin
Singlet oxygen
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Summary:[Display omitted] A synthesis of moracin M using Appel dehydration of a biomimetic inspired endoperoxide and subsequent late stage aromatization, is described. A key 1,3-diene, obtained from a base-free Suzuki-Miyaura coupling, can undergo biomimetic oxidation to its endoperoxide, followed by dehydration under Appel conditions and aromatization to give a benzofuran, with subsequent deprotection then providing moracin M in only 4-steps. Alternatively, this 1,3‑diene can undergo aromatization and subsequent deprotection providing a synthetic route to resveratrol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154273