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Synfacts 2020; 16(05): 0506
DOI: 10.1055/s-0040-1707610
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Isochrysohermidin

Contributor(s):
Erick M. Carreira
,
Moritz J. Classen
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
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Publication History

Publication Date:
20 April 2020 (online)

 
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Key words

isochrysohermidin - 2-oxo-3-pyrroline dimer - inverse electron-demand Diels–Alder reaction - 1O2 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.


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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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