Total synthesis and establishment of the absolute stereochemistry of (+)-mostueine. Addition of chiral nucleophiles to 3,4-dihydro-2-methyl-9-(p-toluenesulfonyl)-β-carbolinium iodide
Total synthesis and establishment of the absolute stereochemistry of (+)-mostueine. Addition of chiral nucleophiles to 3,4-dihydro-2-methyl-9-(p-toluenesulfonyl)-β-carbolinium iodide
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(+)-mostueine 的全合成和绝对立体化学的建立。手性亲核试剂与 3,4-二氢-2-甲基-9-(对甲苯磺酰基)-β-碘化碳的加成。
DOI：
10.1139/v92-374
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发表时间：
1992
影响因子：
1.1
通讯作者：
D. Maclean
中科院分区：
文献类型：
--
作者：
A. Rey;W. Szarek;D. Maclean
本文报道了五环吲哚生物碱（+）-mostueine（1）的高度收敛合成。关键步骤是由（1′S）-3-（1′-羟乙基）-4-甲基吡啶衍生的阴离子（4）与碘化3，4-二氢-2-甲基-9-（对甲苯磺酰基）-β-咔啉鎓盐（3）偶联。在β-咔啉环系的C-1位（摩斯杜因的C-3位）获得了低的不对称诱导（15%de）。非发酵面包酵母介导的3-乙酰基-4-甲基吡啶的还原提供了可接受的产率（67%）和高光学纯度（99.0%ee）的羟乙基吡啶组分。1的合成确定了其绝对立体化学为（3S，19 R）。
A highly convergent synthesis of the pentacyclic indole alkaloid (+)-mostueine (1) is described. The key step involved the coupling of the dianion derived from (1′S)-3-(1′-hydroxyethyl)-4-methylpyridine (4) with the iminium salt 3,4-dihydro-2-methyl-9-(p-toluenesulfonyl)-β-carbolinium iodide (3). Low asymmetric induction (15% de) at the C-1 position of the β-carboline ring system (C-3 of mostueine) was obtained. The nonfermenting baker's yeast-mediated reduction of 3-acetyl-4-methylpyridine provided the hydroxyethylpyridine component in acceptable yield (67%) and high optical purity (99.0% ee). This synthesis of 1 has established that the absolute stereochemistry of mostueine is (3S, 19R).