Tetrahedron p. 2307 - 2322 (1989)
Update date:2022-07-29
Topics:
McIntyre, C. Rupert
Scott, Fiona E.
Simpson, Thomas J.
Trimble, Laird A.
Vederas, John C.
Incorporation of (13)C-labelled acetates and methionine, (14)C and (2)H-labelled ethyl 3,5-dimethylorsellinate into terretonin (5) by cultures of Aspergillus terreus indicated that its biosynthesis proceeds via a mixed polyketide-terpenoid (meroterpenoid) pathway.Incorporation of (18)O2 gas and ethyl 3,5-dimethylorsellinate (7) doubly labelled with (13)C and (18)O in the carbonyl of the carboxyl group and at the C-6 position into terretonin (5) and observation of (18)O isotope-induced shifts in the (13)C n.m.r. spectra and GC/MS studies of the enriched metabolites determined the origin of all of the oxygen atoms in (5) and provided mechanistic insight into the biosynthetic pathway.
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Doi:10.1016/j.tetlet.2009.10.001
(2009)Doi:10.1021/op1000447
(2010)Doi:10.1016/j.bmcl.2013.03.098
(2013)Doi:10.1021/ic100313j
(2010)Doi:10.1021/jm00129a028
(1989)Doi:10.1016/S0040-4039(00)99128-7
(1989)
