Abstract

An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.

An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.

中文翻译：

---

简洁和环保的生物活性的3-羟基-2-哌啶酮生物碱推定结构的不对称全合成

摘要

描述了3-羟基-2-哌啶酮生物碱衍生物的推定结构的立体异构体的不对称全合成。这条路线不仅简洁高效，而且可以通过环保的方式来实现。为此，简单的苄基哌啶的直接和双重C–H氧化反应和贝克酵母中羰基的还原反应使得仅在短时间内即可快速进入光学富集的（S）-1-苄基-3-羟基-2-哌啶酮三个步骤。NMR数据与在第一次总合成中获得的数据一致（与天然产物有所不同），但是，旋光度与天然和合成材料均不匹配。

描述了3-羟基-2-哌啶酮生物碱衍生物的推定结构的立体异构体的不对称全合成。这条路线不仅简洁高效，而且可以通过环保的方式来实现。为此，简单的苄基哌啶的直接和双重C–H氧化反应和贝克酵母中羰基的还原反应使得仅在短时间内即可快速进入光学富集的（S）-1-苄基-3-羟基-2-哌啶酮三个步骤。NMR数据与在第一次总合成中获得的数据一致（与天然产物有所不同），但是，旋光度与天然和合成材料均不匹配。