liberated from the template by retro-Diels–Alder reaction, and converted into
mevalonolactone via an exhaustive oxidation sequence.
Dujardin et al. have reported the synthesis of simple optically pure
mevalonolactone derivatives via a hetero Diels–Alder cycloaddition [92]
(Scheme 48). The lanthanide Lewis acid-catalyzed hetero Diels–Alder cycloaddition of tert-butyloxymethylenepyruvate 230 with a vinyl ether derived from
mandelic acid 231 afforded a cycloadduct, which on hydrogenolysis gave the
saturated adduct 232. This intermediate was then transformed into the
mevalonolactone derivative 234 in a few steps through oxidation of a lactol
intermediate 233.
Scheme 46 Synthesis of (R)-mevalonolactone
Scheme 47 Synthesis of (R)-mevalonolactone
Scheme 48 Synthesis of a mevalonolactone derivative
122
K. Palanichamy and K.P. Kaliappan
mevalonolactone via an exhaustive oxidation sequence.
Dujardin et al. have reported the synthesis of simple optically pure
mevalonolactone derivatives via a hetero Diels–Alder cycloaddition [92]
(Scheme 48). The lanthanide Lewis acid-catalyzed hetero Diels–Alder cycloaddition of tert-butyloxymethylenepyruvate 230 with a vinyl ether derived from
mandelic acid 231 afforded a cycloadduct, which on hydrogenolysis gave the
saturated adduct 232. This intermediate was then transformed into the
mevalonolactone derivative 234 in a few steps through oxidation of a lactol
intermediate 233.
Scheme 46 Synthesis of (R)-mevalonolactone
Scheme 47 Synthesis of (R)-mevalonolactone
Scheme 48 Synthesis of a mevalonolactone derivative
122
K. Palanichamy and K.P. Kaliappan