Total synthesis and absolute configuration determination of (+)-subincanadine F

被引：36

作者：

Chen, Pinhong ^{[1
]}

Cao, Lidong ^{[1
]}

Tian, Wenhai ^{[1
]}

Wang, Xinfeng ^{[1
]}

Li, Chaozhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Synthet Chem Nat Subst, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 44期

基金：

中国国家自然科学基金;

关键词：

RADICAL REACTIONS; ALKALOIDS; CYCLIZATIONS; COMBINATION; ESTERS; IODIDE;

D O I：

10.1039/c0cc03428b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric synthesis of indole alkaloid (+)-subincanadine F was successfully accomplished with the uncommon 7-endo-trig stereoselective radical cyclization as the key step and its absolute configuration was thus assigned.

引用

页码：8436 / 8438

页数：3

共 32 条

[1] Total Synthesis of the Bridged Indole Alkaloid Apparicine [J].

Bennasar, M. -Lluisa ;

Zulaica, Ester ;

Sole, Daniel ;

Roca, Tomas ;

Garcia-Diaz, Davinia ;

Alonso, Sandra .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8359-8368

[2] The first total synthesis of (±)-apparicine [J].

Bennasar, M. -Lluisa ;

Zulaica, Ester ;

Sole, Daniel ;

Alonso, Sandra .

CHEMICAL COMMUNICATIONS, 2009, (23) :3372-3374

[3] p-MeOC6H4N2+BF4-/TiCl3: a novel initiator for halogen atom-transfer radical reactions in aqueous media [J].

Cao, Lidong ;

Li, Chaozhong .

TETRAHEDRON LETTERS, 2008, 49 (52) :7380-7382

[4] Synthesis and structural revision of (±)-laurentristich-4-ol [J].

Chen, Pinhong ;

Wang, Junhua ;

Liu, Kun ;

Li, Chaozhong .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :339-341

[5] Protecting-Group-Free Total Synthesis of (±)-Subincanadine F [J].

Chen, Pinhong ;

Cao, Lidong ;

Li, Chaozhong .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7533-7535

[6] L-tryptophan radical cation electron spin resonance studies: Connecting solution-derived hyperfine coupling constants with protein spectral interpretations [J].

Connor, Henry D. ;

Sturgeon, Bradley E. ;

Mottley, Carolyn ;

Sipe, Herbert J., Jr. ;

Mason, Ronald P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6381-6387

[7] REDOX-INDUCED RADICAL AND RADICAL IONIC CARBON-CARBON BOND-FORMING REACTIONS [J].

DALKO, PI .

TETRAHEDRON, 1995, 51 (28) :7579-7653

[8] Biomimetic entry to the sarpagan family of indole alkaloids:: Total synthesis of (+)-geissoschizine and (+)-N-methylvellosimine [J].

Deiters, A ;

Chen, K ;

Eary, CT ;

Martin, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) :4541-4550

[9] On the 6-exo atom transfer radical cyclization reactions of 3-butenyl 2-iodoalkanoates [J].

Fang, X ;

Xia, HR ;

Yu, H ;

Dong, XC ;

Chen, MB ;

Wang, QR ;

Tao, FG ;

Li, CZ .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8481-8488

[10] Efficient Regio- and Stereoselective Formation of Azocan-2-ones via 8-Endo Cyclization of α-Carbamoyl Radicals [J].

Fang, Xinqiang ;

Liu, Kun ;

Li, Chaozhong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (07) :2274-2283

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