A Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH₄/MeOH or diastereoselective (up to 92:8) SnCl₄/NaBH₄ conditions yielding (1R^∗,3S^∗)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (±)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein.

中文翻译：

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3,6-二氢-1,2-二恶英的多米诺骨牌-德拉邦/氮杂-迈克尔反应及其在神经酰胺转运抑制剂（±）-HPA-12合成中的应用

已经开发了3，6-二氢-1，2-二恶英与伯胺和仲胺的Kornblum-DeLaMare /氮杂-Michael反应，其提供了4-羟基-3-氨基酮。使用非选择性NaBH ₄ / MeOH或非对映选择性（最高达92：8）SnCl ₄ / NaBH ₄条件还原aza-Michael产物，生成（1 R ^∗，3 S ^∗）-3-氨基-1,4-二醇产量分别高达97％和70％。主要还原产物分两步转化为（±）-HPA-12，后者是胞质神经酰胺转运蛋白的抑制剂。