TY - JOUR
T1 - Synthesis and Stereochemical Revision of the Aromatic Polyketide NFAT-133
AU - Sato, Hikaru
AU - Kwon, Eunsang
AU - Taguchi, Yuka
AU - Yoshida, Shinichiro
AU - Kuwahara, Shigefumi
AU - Ogura, Yusuke
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI (No. 17K15264). We thank Dr. H. Watanabe (Agilent Technologies) for his help in measurements of 2D NMR.
Publisher Copyright:
© 2019 American Chemical Society and American Society of Pharmacognosy.
PY - 2019/7/26
Y1 - 2019/7/26
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.jnatprod.8b01063
DO - 10.1021/acs.jnatprod.8b01063
M3 - Article
C2 - 31268714
AN - SCOPUS:85070538817
SN - 0163-3864
VL - 82
SP - 1791
EP - 1796
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 7
ER -