A process is described for the synthesis of kilogram
quantities
of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality
of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural.
Key steps in the synthesis include a Wittig reaction, Piancatelli
rearrangement, and an enzymatic resolution featuring in situ recycling
of the undesired enantiomer furnishing the desired homochiral alcohol
in ≥99.5% ee. As a retort to the unsatisfactory coformation
of about 8% at best of the trans-olefin in the Wittig
reaction, a change to the order of several steps and the identification
of a recrystallisable, amine salt derivative, 2, allowed
the unwanted isomer to be controlled to as low as 0.2%.
The self-assembly of flexible bended dicarboxylate ligand, 2,2 0 -(2,4,6-trimethyl-1,3-phenylene)bis(methylene)-bis(sulfanediyl)dibenzoic acid (H 2 L), with Mn(OAc) 2 $4H 2 O resulted in the formation of a novel metal-organic coordination cage with binuclear manganese SBU as the vertex, which represents the first metalorganic coordination cage constructed from a flexible dicarboxylate ligand and a binuclear SBU.
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