Stereoselective synthesis of tetrahydroisoquinoline alkaloids: (-)-trolline, (+)-crispin A, (+)-oleracein E

被引：34
作者：
Kawai, Nobuyuki [1 ]
Matsuda, Mika [1 ]
Uenishi, Jun'ichi [1 ]
机构：
[1] Kyoto Pharmaceut Univ, Kyoto 6078412, Japan
来源：
TETRAHEDRON | 2011年 / 67卷 / 45期
基金：
日本学术振兴会;
关键词：
Tetrahydroisoquinoline alkaloids; (S)-(-)-Trolline; (R)-(+)-Crispin A; (R)-(+)-Oleracein E; Bi(OTf)(3)-Catalyzed cyclization; 1,3-Chirality transfer reaction; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ISOQUINOLINE; DERIVATIVES; METATHESIS; CARBOLINE; EFFICIENT; IMINES; ACID;
D O I：
10.1016/j.tet.2011.09.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tetrahydroisoquinoline alkaloids, (S)-(-)-trolline, (R)-(+)-crispin A, and (R)-(+)-oleracein E, have been synthesized stereoselectively from the both enantiomers of common intermediate (S)-4 and (R)-4. The key step in the synthesis include a stereoselective Bi(OTf)(3)-catalyzed intramolecular 1,3-chirality transfer reaction of chiral non-racemic amino allylic alcohols (S)-6 and (R)-6 to construct both enantiomers of (E)-1-propenyl tetrahydroisoquinoline 4. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8648 / 8653
页数：6
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