Biomimetic total synthesis and structure confirmation of myrtucommulone K. Issue 19 (10th May 2017)

• Record Type: Journal Article
• Authors: Zhou, Wen-Li; Tan, Hai-Bo; Qiu, Sheng-Xiang; Chen, Guang-Ying; Liu, Hong-Xin; Zheng, Chao
• Is Part Of: Tetrahedron letters. Volume 58:Issue 19(2017)
• Page Start: 1817
• Page End: 1821
• Publication Date: 2017-05-10
• Subjects: Myrtucommulone K -- Biomimetic total synthesis -- Structure revision -- Heteroatom Diels-Alder cycloaddition -- Meroterpenoid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.03.059
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The structure of myrtucommulone K was revised. Its first stereoselective total synthesis was achieved by biomimetic strategy. Enamime-catalyzed Knoevenagel condensation was established to access precursori . The active precursori was successfully characterized by NMR for the first time. Abstract: A confirmed structure of meroterpenoid myrtucommulone K, which is vastly different from the originally reported one, is conducted. The first biomimetic total synthesis towards the assignment of its absolute configuration has been efficiently accessed in 5 steps, and key to the success was a heteroatom Diels-Alder cycloaddition. The structure of myrtucommulone K was re-elucidated and confirmed by extensive spectroscopic interpretation of 1D and 2D NMR.