Synthesis and Stereochemical Revision of the Aromatic Polyketide NFAT-133.
J Nat Prod
; 82(7): 1791-1796, 2019 07 26.
Article
em En
| MEDLINE
| ID: mdl-31268714
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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pentanonas
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Pentanóis
Idioma:
En
Revista:
J Nat Prod
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Japão