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

Bandari Chandrasekhar; Sewon Ahn; Jae Sang Ryu

doi:10.1055/s-0036-1588369

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

Bandari Chandrasekhar, Sewon Ahn, Jae Sang Ryu

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

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.

Original language	English
Article number	ss-2016-f0702-op
Pages (from-to)	1569-1574
Number of pages	6
Journal	Synthesis (Germany)
Volume	49
Issue number	7
DOIs	https://doi.org/10.1055/s-0036-1588369
State	Published - 1 Apr 2017

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2015R1A2A2A01004511 and NRF-2014R1A2A1A11050112).

Publisher Copyright:
© Georg Thieme VerlagStuttgart · New York.

Keywords

4-isoxazoline
gold
HPA-12
nitrone
stereoselective synthesis

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10.1055/s-0036-1588369

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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",

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.",

keywords = "4-isoxazoline, gold, HPA-12, nitrone, stereoselective synthesis",

author = "Bandari Chandrasekhar and Sewon Ahn and Ryu, {Jae Sang}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2015R1A2A2A01004511 and NRF-2014R1A2A1A11050112). Publisher Copyright: {\textcopyright} Georg Thieme VerlagStuttgart · New York.",

year = "2017",

month = apr,

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doi = "10.1055/s-0036-1588369",

language = "English",

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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. / Chandrasekhar, Bandari; Ahn, Sewon; Ryu, Jae Sang.
In: Synthesis (Germany), Vol. 49, No. 7, ss-2016-f0702-op, 01.04.2017, p. 1569-1574.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Chandrasekhar, Bandari

AU - Ahn, Sewon

AU - Ryu, Jae Sang

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2015R1A2A2A01004511 and NRF-2014R1A2A1A11050112). Publisher Copyright: © Georg Thieme VerlagStuttgart · New York.

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N2 - 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.

AB - 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.

KW - 4-isoxazoline

KW - gold

KW - HPA-12

KW - nitrone

KW - stereoselective synthesis

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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

Abstract

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Keywords

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