Chemoenzymatic Synthesis of (-)-Ribisins A and B from Dibenzo[b,d]furan

Derek R. Boyd*, Narain D. Sharma, Christopher J. McGivern, Paul J. Stevenson, Patrick Hoering, Christopher C.R. Allen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
20 Downloads (Pure)

Abstract

cis-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.

Original languageEnglish
Pages (from-to)15165- 15172
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Early online date06 Nov 2019
DOIs
Publication statusPublished - 06 Dec 2019

ASJC Scopus subject areas

  • Organic Chemistry

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