Total synthesis of ent-dihydrocorynantheol by using a proline-catalyzed asymmetric addition reaction
Total synthesis of ent-dihydrocorynantheol by using a proline-catalyzed asymmetric addition reaction
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DOI：
10.1021/ol0530575
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发表时间：
2006-04-13
期刊：
影响因子：
5.2
通讯作者：
Ohsawa, A
中科院分区：
文献类型：
--
作者：
Itoh, T;Yokoya, M;Ohsawa, A
在(S)-脯氨酸存在的情况下，9 - toyl -3,4-二氢- β -carboline与3-乙基-3-丁烯-2- 1反应得到(3R,12bR)-3-乙基-12- toyl - 3,4,6,7,8,9,10,11,2,12b -十氢- 1h -吲哚[2,3-a]喹啉-2- 1，完全对映选择性和非对映选择性。这样得到的化合物很容易在三个步骤中转化为对-二氢紫薇醇。
9-Tosyl-3,4-dihydro-beta-carboline reacted with 3-ethyl-3-buten-2-one in the presence of (S)-proline to give (3R,12bR)-3-ethyl-12-tosyl-3,4,6,7,8,9,10,11,1 2,12b-decahydro-1H-indolo[2,3-a]quinolizin-2-one in complete enantio- and diastereoselectivity. The compound thus obtained was readily transformed to ent-dihydrocorynantheol in three steps.