An approach towards expanding the scope of masked o-benzoquinone dimers to generate diverse compound libraries

被引：7

作者：

Chittimalla, Santhosh Kumar ^{[1
]}

Laxmi, Shoba ^{[2
]}

Liing, Amerlyn Chong Ming ^{[2
]}

Jun, Jerald Lam Kai ^{[2
]}

Kuppusamy, Rajesh ^{[1
]}

Putturu, Sireesha ^{[1
]}

Bandi, Chennakesavulu ^{[1
]}

机构：

[1] AMRI Singapore Res Ctr, Dept Med Chem, Singapore 117525, Singapore

[2] Singapore Polytech, Sch Chem & Life Sci, Singapore 139651, Singapore

来源：

RSC ADVANCES | 2015年 / 5卷 / 37期

关键词：

ROSANE DITERPENES; CONSTITUENTS; (+)-GRANDIFLORACIN; DEAROMATIZATION; SESQUITERPENE; DIMERIZATION; OXIDATION; ACCESS;

D O I：

10.1039/c5ra03627e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this report, a simple and rapid approach for the synthesis of masked o-benzoquinone (MOB) heterodimers is presented. Appropriately substituted 2-methoxyphenols were converted to MOB homodimers which were then transformed to MOB heterodimers utilizing either vinylic substitution (via addition-elimination) reaction protocol or organometallic reaction procedures.

引用

页码：29391 / 29396

页数：6

共 41 条

[1]

[Anonymous], BLACK IMAGINATION SC

[2] NUCLEOPHILIC ATTACKS ON CARBON CARBON DOUBLE-BONDS .34. INTRAMOLECULAR ELEMENT EFFECT IN COMPETITIVE EXPULSION OF 2 HALIDE NUCLEOFUGES AS A TOOL FOR INVESTIGATING THE RAPID STEP OF NUCLEOPHILIC VINYLIC SUBSTITUTION [J].

AVRAMOVITCH, B ;

WEYERSTAHL, P ;

RAPPOPORT, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6687-6697

[3] Antiausterity Agents from Uvaria dac and Their Preferential Cytotoxic Activity against Human Pancreatic Cancer Cell Lines in a Nutrient-Deprived Condition [J].

Awale, Suresh ;

Ueda, Jun-ya ;

Athikomkulchai, Sirivan ;

Abdelhamed, Sherif ;

Yokoyama, Satoru ;

Saiki, Ikuo ;

Miyatake, Ryuta .

JOURNAL OF NATURAL PRODUCTS, 2012, 75 (06) :1177-1183

[4] Antifungal rosane diterpenes and other constituents of Hugonia castaneifolia [J].

Baraza, Lilechi D. ;

Joseph, Cosam C. ;

Munissi, Joan J. E. ;

Nkunya, Mayunga H. H. ;

Arnold, Norbert ;

Porzel, Andrea ;

Wessjohann, Ludger .

PHYTOCHEMISTRY, 2008, 69 (01) :200-205

[5] Recent Advances in Our Mechanistic Understanding of SNV Reactions [J].

Bernasconi, Claude F. ;

Rappoport, Zvi .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :993-1003

[6] Progress toward the total synthesis of bacchopetiolone:: Application of a tandem aromatic oxidation/Diels-Alder reaction [J].

Berube, Amelie ;

Drutu, Ioana ;

Wood, John L. .

ORGANIC LETTERS, 2006, 8 (24) :5421-5424

[7] 3,10-DIHYDROXYDIELMENTHA-5,11-DIENE-4,9-DIONE - A DITERPENOID (BISMONOTERPENOID) WITH A NOVEL CARBON SKELETON [J].

CARMAN, RM ;

LAMBERT, LK ;

ROBINSON, WT ;

VANDONGEN, JMAM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (11) :1843-1850

[8]

CHEN YP, 1972, TETRAHEDRON LETT, P1607

[9] Palladium-Catalyzed Regioselective Synthesis of Oxygenated Biphenyls [J].

Chittimalla, Santhosh Kumar ;

Kuppusamy, Rajesh ;

Akavaram, Naresh .

SYNLETT, 2015, 26 (05) :613-618

[10] A two step protocol for the synthesis of highly substituted benzobicyclo[2.2.2]octadienone derivatives from 2-methoxyphenols [J].

Chittimalla, Santhosh Kumar ;

Bandi, Chennakesavulu ;

Putturu, Sireesha .

RSC ADVANCES, 2015, 5 (11) :8050-8055

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