Total synthesis of pteridic acids A and B

Takashi Nakahata, Shohei Fujimura, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4584-4593
Number of pages10
JournalChemistry - A European Journal
Volume12
Issue number17
DOIs
Publication statusPublished - 2006 Jun 2

Keywords

  • Aldol reaction natural products
  • Polyketides
  • Pteridic acid
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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