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Total Synthesis of Isochrysohermidin
d,l- and meso-Isochrysohermidin: Total Synthesis and Interstrand DNA Cross-Linking.
J. Am. Chem. Soc. 1993;
20 April 2020 (online)
Key wordsisochrysohermidin - 2-oxo-3-pyrroline dimer - inverse electron-demand Diels–Alder reaction - 1O2 cycloaddition
In 1993, Boger and Baldino described a concise synthesis of isochrysohermidin, a 2-oxo-3-pyrroline dimer first isolated from Mercuralis leiocarpa. Through their synthetic efforts, they were able to show the interstrand DNA cross-linking capabilities of isochrysohermidin.
C is accessed from A by an inverse-electron-demand Diels–Alder cycloaddition with B and is further elaborated to D by reductive ring contraction. meso- and d,l-isochrysohermidin are obtained by a singlet oxygen cycloaddition, followed by in situ decarboxylation.