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2005
Terpenes
U 0200
23- 196
A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically
Controlled Ring-Closing Metathesis Reaction of a Densely Functionalized Diene.
— Key step in the synthesis of title compound (I) is the ring-closing metathesis of highly functionalized diene (II) which unexpectedly furnishes the less stable E-isomer (III).
After removal of the anisyl groups and subsequent oxidation of the allylic diol, the
resulting enedione isomerizes readily to the stable Z-isomer (not shown). —
(CASTOLDI, D.; CAGGIANO, L.; PANIGADA, L.; SHARON, O.; COSTA, A. M.;
GENNARI*, C.; Angew. Chem., Int. Ed. 44 (2005) 4, 588-591; Dip. Chim. Org. Ind.,
Univ. Stud. Milano, CNR, I-20133 Milano, Italy; Eng.) — Nuesgen
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