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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)
Author(s) -
Crisp Antony L.,
Noble Benjamin,
Schwartz Brett D.,
Willis Anthony C.,
Coote Michelle L.,
Banwell Martin G.
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900404
Subject(s) - trimethylenemethane , chemistry , cycloaddition , tropolone , carbocation , iminium , adduct , benzopyran , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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. on page 1458 in Issue 8, 2019 (DOI: 10.1002/ajoc.201900334).