Boger DL.
*
Baldino CM.
The Scripps Research Institute, La Jolla, USA
d,
l- and
meso-Isochrysohermidin: Total Synthesis and Interstrand DNA Cross-Linking.
J. Am. Chem. Soc. 1993;
115: 11418-11425
Key words
isochrysohermidin - 2-oxo-3-pyrroline dimer - inverse electron-demand Diels–Alder
reaction -
1O
2 cycloaddition
Significance
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.
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.
