文献类型：期刊文献

英文题名：Synthesis of tadalafil (Cialis) from L-tryptophan

作者：Xiao, Sen[1];Shi, Xiao-Xin[1];Xing, Jing[1];Yan, Jing-Jing[1];Liu, Shi-Ling[1];Lu, Wei-Dong[1]

机构：[1]E China Univ Sci & Technol, Dept Pharmaceut Engn, Sch Pharm, Shanghai 200237, Peoples R China

年份：2009

卷号：20

期号：18

起止页码：2090

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000271252000003)】；

基金：We thank the Chinese National Science Foundation (No. A-20172015) and Shanghai Educational Development Foundation (The Dawn Program No. 03SG27) for the financial support of this work

语种：英文

摘要：The first synthesis of tadalafil 1 (Cialis) from L-tryptophan is described The title compound 1 was synthesized via seven steps from L-tryptophan methyl ester hydrochloride in 42 3% overall yield Two characteristic steps involved in this synthesis are the base-catalyzed epimerization of the C-3 position of (1S,3S)-1,2,3-trisubstituted-tetrahydro-beta-carboline 3a and the acid-catalyzed epimerization of the C-1 position of (1S,3R)-1,3-disubstituted-tetraliydro-beta-carboline 5. The (S)-configurations at C-1 and C-3 were inverted to (R)-configurations during the epimerization reactions. The base-catalyzed epimerization of C-3 of (1S,3S)-1,2,3-trisubstituted-tetrahydro-beta-carbolines 3a-3e was also studied in detail. (C) 2009 Elsevier Ltd All rights reserved