Organic Letters
Letter
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Scheme 6. Synthesis of the N-Phenyltetrazolylsulfone 5
́
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O-desilylation and brief treatment (0.5 h) with K2CO3 (1 equiv)
in MeOH at 0 °C. Following final purification by SiO2 flash
chromatography, the natural product was obtained in 70% yield
for the two steps and was spectroscopically identical with the
spectra reported for (+)-brefeldin A in the literature in CD3OD2f
and CDCl3.20 Cleavage of the O-silyl protecting groups from 41
with n-Bu4NF in THF afforded 4-epi-brefeldin A,2h as well.
In summary, a new total synthesis of (+)-brefeldin A was
achieved from the Padwa [3 + 2]-cycloadduct 13. The utility of
the latter cycloaddition was demonstrated for the preparation of
trans-configured chiral cyclopentanes. New types of brefeldin
analogues should now prove accessible.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Full experimental procedures for all steps, as well as copies
1
of the IR, HMRS, and H/13C NMR spectra of every
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank QUB for a studentship and for funding this work.
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Chem. Soc. Jpn. 1979, 52, 1989.
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