1434278-12-2Relevant academic research and scientific papers
Chemoenzymatic asymmetric total synthesis of (R)-lasiodiplodin methyl ether through a sulfatase-based deracemization process
Fuchs, Michael,Toesch, Michael,Schober, Markus,Wuensch, Christiane,Faber, Kurt
, p. 356 - 361 (2013/03/13)
(R)-Lasiodiplodin methyl ether, a precursor of the antileukemic agent lasiodiplodin, was synthesized through a seven-step linear sequence. Chirality was introduced through a sulfatase-based deracemization process, in which a functionalized (rac)-sec-sulfate ester was enzymatically hydrolyzed with inversion of the stereocenter using an alkyl sulfatase. The remaining sulfate ester enantiomer was hydrolyzed with retention of configuration under acidic conditions, yielding the chiral key building block as the sole product in 93 % ee The total synthesis was completed through Negishi cross-coupling and ring-closing metathesis.
