Pteridic acid A (1) is a spirocyclic octaketide produced by the phytoepiphytic actinomycete Streptomyces hygroscopicus TP-A0451 and possesses potent plant-growth-promoting activity comparable to that of indole-3-acetic acid. The enantioselective total synthesis of this natural product was achieved by employing the Sn(OTf)2-mediated Evans aldol reaction and the Fukuyama acetylenic coupling reaction as the key C-C bond-forming steps producing 1 through a 14-step sequence in 22% overall yield from a known oxazolidinone derivative. MgBr2-mediated equilibration of an anomerically favored spirocyclic intermediate used for the synthesis of 1 brought about partial epimerization of the spirocenter to give the corresponding anomerically disfavored epimer, which was converted into pteridic acid B (11-epi-1), another plant-growth promoter of the same microbial origin.
- Aldol reaction natural products
- Pteridic acid
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry