Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine

被引：46

作者：

Ding, Ming ^{[1
,2
,3
]}

Liang, Kangjiang ^{[2
,3
]}

Pan, Rui ^{[2
]}

Zhang, Hongbin ^{[1
]}

Xia, Chengfeng ^{[1
,2
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resources, Kunming 650091, Peoples R China

[2] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期

基金：

中国国家自然科学基金;

关键词：

CONCISE TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; (+)-WIN 64821; DIMERIZATION; CHIMONANTHINE; CONFIGURATION; DERIVATIVES; ALLYLATION; ARYLATION; INDOLES;

D O I：

10.1021/acs.joc.5b01907

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (-)-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the chimonanthine skeleton to the calycanthine skeleton was observed and facilitated the synthesis of (-)-calycanthine (3).

引用

页码：10309 / 10316

页数：8