Total synthesis of akuammiline alkaloid (+)-strictamine

被引：20
|
作者：
Chen, Zhi-Tao [1 ]
Xiao, Tao [1 ]
Tang, Pei [1 ]
Zhang, Dan [2 ]
Qin, Yong [2 ]
机构：
[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Minist Educ, Key Lab Drug Targeting & Novel Delivery Syst, Chengdu 610041, Sichuan, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Akuammiline aklaloids; Strictamine; Total synthesis; Johnson-Claisen rearrangement; FORMAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; ALSTONIA-SCHOLARIS; INDOLE ALKALOIDS; MEDIATED CYCLIZATION; STRICTAMINE; (+/-)-STRICTAMINE; (+/-)-ASPIDOPHYLLINE; (+)-SCHOLARISINE;
D O I：
10.1016/j.tet.2018.01.034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric total synthesis of the akuammiline alkaloid (+)-strictamine is described. The key steps of the synthetic route involve an improved Johnson-Claisen rearrangement to facilitate the formation of the challenging C15-C20 linkage and the (E)-alkene side chain, intramolecular nucleophilic substitution cyclization to establish the E ring and diastereoselective Brown hydroboration of the terminal alkene to introduce the C16 stereocenter. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1129 / 1134
页数：6
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