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.

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.

中文翻译：

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通过金（I）催化的炔丙基N-羟胺的环化反应，立体选择性合成神经酰胺转运蛋白（CERT）依赖性神经酰胺贩运抑制剂（1R，3S）-HPA-12。

摘要

使用金（I）催化的炔丙基N-羟胺的环化反应可有效合成神经酰胺转运蛋白（CERT）依赖性的神经酰胺贩运抑制剂HPA-12 ，后者是通过立体选择性硝酮-炔烃加成反应制备的。通过立体选择性还原和还原性开环将所得的4-异恶唑啉转化为合成-1，3-氨基醇。

使用金（I）催化的炔丙基N-羟胺的环化反应可有效合成神经酰胺转运蛋白（CERT）依赖性的神经酰胺贩运抑制剂HPA-12 ，后者是通过立体选择性硝酮-炔烃加成反应制备的。通过立体选择性还原和还原性开环将所得的4-异恶唑啉转化为合成-1，3-氨基醇。