Recent Advances in the Total Synthesis of Prenylflavonoid and Related Diels-Alder Natural Products

被引：33

作者：

Han, Jianguang ^{[1
]}

Jones, Alexander X. ^{[2
,3
]}

Lei, Xiaoguang ^{[2
,3
,4
]}

机构：

[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

[2] Peking Univ, Coll Chem & Mol Engn,Beijing Natl Lab Mol Sci, Synthet & Funct Biomol Ctr,Key Lab Bioorgan Chem, Dept Biol Chem,Minist Educ, Beijing 100871, Peoples R China

[3] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

[4] NIBS, Beijing 102206, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 11期

关键词：

prenylflavonoids; total synthesis; Diels-Alder cycloaddition; biomimetic synthesis; asymmetric synthesis; CULTIVATED MULBERRY TREE; MORUS-ALBA L; ROOT BARK; BROSIMOPSIS-OBLONGIFOLIA; NANOPARTICLE CATALYSIS; MORACEOUS PLANTS; SINGLET OXYGEN; ENE REACTION; KUWANON-H; CONSTITUENTS;

D O I：

10.1055/s-0034-1378696

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review summarizes the application of different strategies for the key Diels-Alder cycloaddition in prenylflavonoid and related Diels-Alder natural products synthesis, highlighting the application of novel methodologies and innovative strategies in the synthesis of these natural products and their analogues. 1 Introduction 2 Classical Conditions for the Diels-Alder Cycloaddition 2.1 Thermal Promotion 2.2 High-Pressure Promotion 2.3 Bronsted Acid Catalysis 3 Modern Approaches to the Diels-Alder Cycloaddition 3.1 Electron-Transfer Initiation 3.2 Silver-Nanoparticle Catalysis 3.3 Chiral-Boron-Complex Promotion 4 Conclusion

引用

页码：1519 / 1533

页数：15

共 52 条

[1] (1R)-(+)-Camphor and Acetone Derived α′-Hydroxy Enones in Asymmetric Diels-Alder Reaction: Catalytic Activation by Lewis and Bronsted Acids, Substrate Scope, Applications in Syntheses, and Mechanistic Studies [J].

Banuelos, Patricia ;

Garcia, Jesus M. ;

Gomez-Bengoa, Enrique ;

Herrero, Ada ;

Odriozola, Jose M. ;

Oiarbide, Mikel ;

Palomo, Claudio ;

Razkin, Jesus .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1458-1473

[2] Synthetic studies towards the mulberry Diels-Alder adducts: H-bond accelerated cycloadditions of chalcones [J].

Boonsri, Sompong ;

Gunawan, Christian ;

Krenske, Elizabeth H. ;

Rizzacasa, Mark A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (30) :6010-6021

[3] Synthesis of (±)-kuwanon V and (±)-dorsterone methyl ethers via Diels-Alder reaction [J].

Chee, Chin Fei ;

Lee, Yean Kee ;

Buckle, Michael J. C. ;

Rahman, Noorsaadah Abd .

TETRAHEDRON LETTERS, 2011, 52 (15) :1797-1799

[4] An efficient synthesis of (±)-panduratin A and (±)-isopanduratin A, inhibitors of dengue-2 viral activity [J].

Chee, Chin Fei ;

Abdullah, Iskandar ;

Buckle, Michael J. C. ;

Abd Rahman, Noorsaadah .

TETRAHEDRON LETTERS, 2010, 51 (03) :495-498

[5] Electron transfer-initiated Diels-Alder cycloadditions of 2′-hydroxychalcones [J].

Cong, Huan ;

Ledbetter, Dustin ;

Rowe, Gerard T. ;

Caradonna, John P. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9214-+

[6] Total Synthesis of (±)-Sorocenol B Employing Nanoparticle Catalysis [J].

Cong, Huan ;

Porco, John A., Jr. .

ORGANIC LETTERS, 2012, 14 (10) :2516-2519

[7] Chemical Synthesis of Complex Molecules Using Nanoparticle Catalysis [J].

Cong, Huan ;

Porco, John A., Jr. .

ACS CATALYSIS, 2012, 2 (01) :65-70

[8] Silver Nanoparticle-Catalyzed Diels-Alder Cycloadditions of 2′-Hydroxychalcones [J].

Cong, Huan ;

Becker, Clinton F. ;

Elliott, Sean J. ;

Grinstaff, Mark W. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7514-7518

[9] New Diels-Alder type adducts from Morus macroura and their anti-oxidant activities [J].

Dai, SJ ;

Wu, Y ;

Wang, YH ;

He, WY ;

Chen, RY ;

Yu, DQ .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (10) :1190-1193

[10]

Deshpande V. H., 1983, TETRAHEDRON LETT, V24, P3013

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