Concise synthesis of moracin M using Appel mediated dehydration of a bioinspired endoperoxide. (12th January 2023)

• Record Type: Journal Article
• Authors: Al-Jawaheri, Yassir; Elsegood, Mark R.J.; Mistry, Jai-Ram; Kimber, Marc C.
• Is Part Of: Tetrahedron letters. Volume 114(2023)
• Publication Date: 2023-01-12
• Subjects: Benzofuran -- Endoperoxide -- Biomimetic -- Moracin -- Singlet oxygen; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154273
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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.