Synthetic Studies toward the Myrioneuron Alkaloids

被引:1
作者
Aquilina, Jake M. [1 ]
Smith, Myles W. [1 ]
机构
[1] UT Southwestern, Med Ctr, 5323 Harry Hines Blvd, Dallas, TX 75390 USA
来源
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 22期
基金
美国国家卫生研究院;
关键词
alkaloids; total synthesis; Myrioneuron; asymmetric synthesis; biosynthesis; FUSED OCTAHYDROQUINOLIZINE ALKALOIDS; DIPOLAR CYCLOADDITION CASCADE; ACYCLIC ALDEHYDES; TRICYCLIC AMINES; SKELETON; CYCLIZATION; EFFICIENT; CONDENSATION; MYRIBERINE; UNITS;
D O I
10.1055/a-2085-5934
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Myrioneuron alkaloids are a relatively small family of plant-derived alkaloids that present an intriguing array of structural intricacy and biological properties. As such, these natural products have drawn interest from the synthetic community, resulting in creative total syntheses of several family members. This review showcases recent synthetic efforts towards these polycyclic alkaloids. 1 Introduction 1.1 Biological Activity 1.2 Proposed Biosynthesis 2 Synthetic Studies toward the Myrioneuron Alkaloids 2.1 Total Synthesis of Myrioxazines A and B 2.2 Total Synthesis of Myrionine, Myrionidine, and Schoberine 2.3 Total Synthesis of Myrifabrals A and B 2.4 Total Synthesis of Myrioneurinol 3 Conclusions and Outlook
引用
收藏
页码:3725 / 3736
页数:12
相关论文
共 43 条
[1]   Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis-Decahydroquinolines [J].
Amat, Mercedes ;
Ghirardi, Elena ;
Navio, Laura ;
Griera, Rosa ;
Llor, Nuria ;
Molins, Elies ;
Bosch, Joan .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (47) :16044-16049
[2]   Symmetry-Driven Total Synthesis of Myrioneurinol [J].
Aquilina, Jake M. ;
Smith, Myles W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (25) :11088-11093
[3]   Efficient synthesis of bicyclo[3.2.1]octane-2,4-diones and their incorporation into potent HPPD inhibitors [J].
Baalouch, Myriam ;
De Mesmaeker, Alain ;
Beaudegnies, Renaud .
TETRAHEDRON LETTERS, 2013, 54 (06) :557-561
[4]   The enantioselective Tsuji allylation [J].
Behenna, DC ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045
[5]   Stereoselective Formation of Fused Tricyclic Amines from Acyclic Aldehydes by a Cascade Process Involving Condensation, Cyclization, and Dipolar Cycloaddition [J].
Burrell, Adam J. M. ;
Coldham, Iain ;
Watson, Luke ;
Oram, Niall ;
Pilgram, Christopher D. ;
Martin, Nathaniel G. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2290-2300
[6]   Synthesis of Fused Tricyclic Amines from Enolizable Acyclic Aldehydes by Cyclization then Dipolar Cycloaddition Cascade: Synthesis of Myrioxazine A [J].
Burrell, Adam J. M. ;
Coldham, Iain ;
Oram, Niall .
ORGANIC LETTERS, 2009, 11 (07) :1515-1518
[7]   New findings of cyclohexane-fused octahydroquinolizine alkaloids from Myrioneuron faberi [J].
Cao, Ming-Ming ;
Zhang, Jia-Hui ;
Zhang, Yu ;
Peng, Zong-Gen ;
Jiang, Jian-Dong ;
Hao, Xiao-Jiang .
TETRAHEDRON LETTERS, 2016, 57 (50) :5632-5635
[8]   Three new alkaloids from Myrioneuron faberi [J].
Cao, Ming-Ming ;
Zhang, Yu ;
Huang, Sheng-Dian ;
Peng, Zong-Gen ;
Jiang, Jian-Dong ;
Hao, Xiao-Jiang .
TETRAHEDRON LETTERS, 2016, 57 (36) :4021-4023
[9]   Schoberine B, an alkaloid with an unprecedented straight C5 side chain, and myriberine B from Myrioneuron faberi [J].
Cao, Ming-Ming ;
Zhang, Yu ;
Peng, Zong-Gen ;
Jiang, Jian-Dong ;
Gao, Yue-Jiao ;
Hao, Xiao-Jiang .
RSC ADVANCES, 2016, 6 (12) :10180-10184
[10]   Alkaloids with Different Carbon Units from Myrioneuron faberi [J].
Cao, Ming-Ming ;
Zhang, Yu ;
Huang, Sheng-Dian ;
Di, Ying-Tong ;
Peng, Zong-Gen ;
Jiang, Jian-Dong ;
Yuan, Chun-Mao ;
Chen, Duo-Zhi ;
Li, Shun-Lin ;
He, Hong-Ping ;
Hao, Xiao-Jiang .
JOURNAL OF NATURAL PRODUCTS, 2015, 78 (11) :2609-2616