Synthesis 2017; 49(07): 1569-1574
DOI: 10.1055/s-0036-1588369
paper
© Georg Thieme Verlag Stuttgart · New York

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
College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea   Email: ryuj@ewha.ac.kr
,
Sewon Ahn
College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea   Email: ryuj@ewha.ac.kr
,
Jae-Sang Ryu*
College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea   Email: ryuj@ewha.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 06 October 2016

Accepted after revision: 11 November 2016

Publication Date:
13 December 2016 (online)


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.

Supporting Information

 
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