Synthesis and Stereochemical Revision of the Aromatic Polyketide NFAT-133

Hikaru Sato, Eunsang Kwon, Yuka Taguchi, Shinichiro Yoshida, Shigefumi Kuwahara, Yusuke Ogura

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

NFAT-133, isolated from Streptomyces sp., is an immunosuppressive, antidiabetic, and antitrypanosomal aromatic polyketide with three contiguous stereocenters. The first enantioselective total synthesis of the proposed structure of NFAT-133 [(10R,11R,12S)-1] and its C10 epimer [(10S,11R,12S)-1] was achieved from a known aromatic ester (5) by a 10-step sequence that featured chiral auxiliary-directed asymmetric alkylation and the Evans asymmetric aldol reaction as the chirality-inducing steps. The 1H and 13C NMR data as well as the specific rotation value of natural NFAT-133 were not identical to those of the proposed structure, but were in good agreement with those of its C10 epimer. This led us to conclude that the absolute configuration of NFAT-133 should be revised to 10S, 11R, and 12S.

Original languageEnglish
Pages (from-to)1791-1796
Number of pages6
JournalJournal of Natural Products
Volume82
Issue number7
DOIs
Publication statusPublished - 2019 Jul 26

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and Stereochemical Revision of the Aromatic Polyketide NFAT-133'. Together they form a unique fingerprint.

Cite this