Total Synthesis of (±)-Decinine via an Oxidative Biaryl Coupling with Defined Axial Chirality

被引：30

作者：

Shan, Zhen-Hua ^{[3
,4
]}

Liu, Ji ^{[3
,4
]}

Xu, Ling-Min ^{[3
,4
]}

Tang, Ye-Feng ^{[1
,2
]}

Chen, Jia-Hua ^{[3
,4
]}

Yang, Zhen ^{[3
,4
]}

机构：

[1] Tsinghua Univ, Sch Life Sci, Comprehens AIDS Res Ctr, Beijing 100084, Peoples R China

[2] Tsinghua Univ, Sch Med, Beijing 100084, Peoples R China

[3] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, BNLMS,Coll Chem, Beijing 100871, Peoples R China

[4] Peking Univ, Peking Tsinghua Ctr Life Sci, Coll Chem, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 14期

基金：

美国国家科学基金会;

关键词：

LYTHRACEAE ALKALOIDS; ASYMMETRIC-SYNTHESIS; HEIMIA SALICIFOLIA; GOLD CATALYSIS; BIOSYNTHESIS; TRANS-4-(3,4-DIHYDROXYPHENYL)-QUINOLIZIDIN-2-ONE; QUINOLIZIDINE; ASSIGNMENT; REAGENTS; DECODON;

D O I：

10.1021/ol3015573

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-decinine has been achieved. The key steps in the synthesis involved the formation of lasubine II via a gold catalyzed annulation of 1-(but-3-yn-1-yl)piperidine and the formation of the 12-membered ring of decinine (1) with complementary atropselectivity via a VOF3-mediated oxidative biaryl coupling reaction.

引用

页码：3712 / 3715

页数：4

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