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

页码：1129 / 1134

页数：6

共 56 条

[1]

Adams Gregory L, 2016, Alkaloids Chem Biol, V76, P171, DOI 10.1016/bs.alkal.2015.08.001

[2] Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A [J].