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Synfacts 2020; 16(05): 0506
DOI: 10.1055/s-0040-1707610
DOI: 10.1055/s-0040-1707610
Synthesis of Natural Products and Potential Drugs
Total Synthesis of Isochrysohermidin
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. April 2020 (online)
Key words
isochrysohermidin - 2-oxo-3-pyrroline dimer - inverse electron-demand Diels–Alder reaction - 1O2 cycloadditionSignificance
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.
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Comment
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.
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