Front Cover: The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from α‐Tropolone O‐Methyl Ether and Trimethylenemethane (Asian J. Org. Chem. 8/2019). Issue 8 (8th August 2019)

• Record Type: Journal Article
• Authors: Crisp, Antony L.; Noble, Benjamin; Schwartz, Brett D.; Willis, Anthony C.; Coote, Michelle L.; Banwell, Martin G.
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 8(2019)
• Page Start: 1141
• Page End: 1141
• Publication Date: 2019-08-08
• Subjects: [6+3] cycloaddition -- oxidation -- rearrangement -- trimethylenemethane -- troponoid; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900404
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract : A mono‐oxide of the adduct derived from the [6+3] cycloaddition reaction between trimethylenemethane and 2‐methoxytropone undergoes an acid‐catalyzed rearrangement cascade to give, in a first step, a 3‐homoadamantyl carbocation that itself fragments to afford a poly‐substituted bicyclo[4.3.1]decane. This final product embodies key structural elements associated with the tetracyclic alkaloid lycojaponicumin D. The work highlights the potential utility of cycloaddends derived from the higher‐order cycloaddition reactions of troponoids in the synthesis of complex molecular frameworks. More information can be found in the Full Paper by Martin G. Banwell et al. onpage 1458 in Issue 8, 2019 (DOI:10.1002/ajoc.201900334 ).