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Stereoselective Synthesis of a Ceramide Transporter Protein (CERT)-Dependent Ceramide-Trafficking Inhibitor, (1R,3S)-HPA-12, via Gold(I)-Catalyzed Cyclization of a Propargylic N-Hydroxylamine

Title
Stereoselective Synthesis of a Ceramide Transporter Protein (CERT)-Dependent Ceramide-Trafficking Inhibitor, (1R,3S)-HPA-12, via Gold(I)-Catalyzed Cyclization of a Propargylic N-Hydroxylamine
Authors
Chandrasekhar, BandariAhn, SewonRyu, Jae-Sang
Ewha Authors
류재상
SCOPUS Author ID
류재상scopus
Issue Date
2017
Journal Title
SYNTHESIS-STUTTGART
ISSN
0039-7881JCR Link1437-210XJCR Link
Citation
vol. 49, no. 7, pp. 1569 - 1574
Keywords
HPA-12goldnitrone4-isoxazolinestereoselective synthesis
Publisher
GEORG THIEME VERLAG KG
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
A ceramide transporter protein (CERT)-dependent ceramide-trafficking inhibitor, HPA-12, is efficiently synthesized using gold(I)-catalyzed cyclization of a propargylic N-hydroxylamine, which is prepared via a stereoselective nitrone-alkyne addition reaction. The resulting 4-isoxazoline is converted into a syn-1,3-amino alcohol through stereoselective reduction and reductive ring opening.
DOI
10.1055/s-0036-1588369
Appears in Collections:
약학대학 > 약학과 > Journal papers
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