Total Synthesis of Brevenal

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Total Synthesis of Brevenal
Jon D. Rainier Department
of Chemistry, University of Utah.
J. Am. Chem. Soc. 2011, 133, 32083216
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Dinoflagellate-derived marine ladder
toxin Interesting pentacyclic structure Fused
ether architectures
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Olefinic Ester and Diene Ring-Closing Metathesis
Using a Reduced Titanium Alkylidene
J. AM. CHEM. SOC. 2007, 129, 12604-12605
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Rubottom oxidation
Synthesis of Brevenals E-Ring Precursor
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A Novel Carbon-Carbon Bond-Forming Reaction of
Triflates with Copper(1)-Catalyzed Grignard
Reagents
One-pot double alkylation strategy.
J. Org. Chem. 1990, 55,4417422.
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34 was isolated as an inseparable mixture of
diastereomers as a result of the poor selectivity
in the epoxidation reaction made this approach
untenable and forced us to modify our strategy.
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model bicyclic enol ether
39 comes from the oxidation of ZnMe2 by the
epoxide from 31 and the subsequent transfer of
methoxide to the epoxide
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Tetrahedron Letters 51 (2010) 39603961
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lithium di-t-butyl biphenylide (LiDBB)
our spectroscopic data for 49 did not match that
previously reported. While not definitively establ
ished, we presume that pentacycle 49 differs from
the brevenal core at C(23).
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Brevenal Retrosynthesis-2
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From 20 to 55
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