Total Synthesis of (-)-Conolutinine

被引：36

作者：

Feng, Xiangyang ^{[1
,2
]}

Jiang, Guangde ^{[2
]}

Xia, Zilei ^{[2
]}

Hu, Jiadong ^{[1
,2
]}

Wan, Xiaolong ^{[3
]}

Gao, Jin-Ming ^{[1
]}

Lai, Yisheng ^{[2
]}

Xie, Weiqing ^{[1
,3
]}

机构：

[1] Northwest A&F Univ, Coll Sci, Shaanxi Key Lab Nat Prod & Chem Biol, Yang Iing 712100, Shaanxi, Peoples R China

[2] China Pharmaceut Univ, Ctr Drug Discovery, State Key Lab Nat Medicines, Jiangsu Key Lab Drug Discovery Metab Dis, Nanjing 210009, Jiangsu, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 18期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; IMINIUM ION CYCLIZATION; CONCISE TOTAL-SYNTHESIS; SCALABLE SYNTHESIS; MOLECULAR-OXYGEN; (+/-)-MINFIENSINE; REARRANGEMENT; AKUAMMILINE; VINBLASTINE; MINFIENSINE;

D O I：

10.1021/acs.orglett.5b02046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective synthesis of (-)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac)(2) was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (-)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.

引用

页码：4428 / 4431

页数：4

共 38 条

[1]

Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9

[2]

Cordell G.A., 1981, ALKALOIDS, V20, P3

[3] TOTAL SYNTHESIS OF +/-N-METHYLMAYSENINE [J].