A flexible
and convergent strategy for the stereoselective total
synthesis of bioactive marine natural product cytospolide Q has been
developed. The key features of this synthesis include Evans anti-aldol
reaction for the installation of C-2 and C-3 stereocenters and cycloetherification
via epoxide opening followed by concomitant lactonization for the
construction of tetrahydrofuran and γ-butyrolactone scaffolds.
This synthetic study also revealed that protected oxygenated functionality
(methyl ester or benzyl ether) at C-1 position participated readily
in epoxide opening.
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