jo9b02171_si_001.pdf (1.48 MB)
Chemoenzymatic Synthesis of (−)-Ribisins A and B from Dibenzo[b,d]furan
journal contribution
posted on 2019-11-18, 16:06 authored by Derek R. Boyd, Narain D. Sharma, Christopher J. McGivern, Paul J. Stevenson, Patrick Hoering, Christopher C.
R. Allencis-Dihydrodiols, derived from monocyclic
aromatic
compounds, are valuable chiral pool intermediates for the synthesis
of cyclic natural products. A drawback of this approach, to the synthesis
of polycyclic secondary metabolites, is that additional rings must
be annulated. To date, relatively few chiral natural products have
been synthesized from polycyclic arene cis-dihydrodiols.
Fungal metabolites, (−)-ribisins A and B, have now been obtained
by functional group manipulation of a tricyclic arene metabolite,
obtained from toluene dioxygenase-catalyzed regioselective and stereoselective cis-dihydroxylations of dibenzo[b,d]furan.
The synthetic sequences were marginally shorter than the alternative
routes, using monocyclic arene cis-dihydrodiols,
and required no carbon–carbon bond-forming reactions.