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Direct Stereocontrolled Synthesis of Polyoxygenated Hydrobenzofurans and Hydrobenzopyrans from p-Peroxy Quinols
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An acidic-basic tandem cata
lytic process on
p-peroxy quino
ls with hydroxy a
lky
l chains at C-4 a
llowed the one-pot synthesis of hydrobenzofuranand hydrobenzopyran tricyc
lic epoxides. In this transformation, two new cyc
les and four new stereogenic centers are created in a high
lystereocontro
lled manner. The usefu
lness of the strategy is i
llustrated with the first tota
l synthesis and structura
l revision of natura
l productC
leroindicin D.
