posted on 2022-01-10, 16:06authored byTabitha
T. Schempp, Michael J. Krische
The total synthesis of soraphen A,
a myxobacterial metabolite
and inhibitor of acetyl CoA carboxylase, was completed in 11 steps
(longest linear sequence), less than half the steps previously required.
Seven metal-catalyzed processes were deployed to unlock step-economy
(comprising five asymmetric processes and four C–C bond formations).
The present route does not utilize chiral auxiliaries, and four of
five C–C bond formations exploit non-premetalated partners.
To maximize convergency, an asymmetric Tsuji reduction was developed
using a Pd-AntPhos catalyst that allows a metathesis-inactive allylic
carbonate to serve as a masked terminal olefin, thereby enabling successive
olefin metathesis events.