Total syntheses of (+)-lyconadin A and (-)-lyconadin B

被引：71

作者：

Beshore, Douglas C.

Smith, Amos B., III ^{[1
]}

机构：

[1] Univ Penn, Lab Res Struct Matter, Dept Chem, Philadelphia, PA 19104 USA

[2] Univ Penn, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 14期

关键词：

D O I：

10.1021/ja070336+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective syntheses of (+)-lyconadin A and (-)-lyconadin B are described. Key bond constructions include a strategy-level intramolecular aldol/conjugate addition cascade, an olefin aminoiodination, and a novel one-pot alpha-pyridinone annulation.

引用

收藏

页码：4148 / +

页数：3

相关论文

共 16 条

[1] SULFURANES .6. REACTIONS INVOLVING ALKOXY LIGANDS OF DIALKOXYDIARYLSULFURANES - FORMATION OF OLEFINS AND ETHERS [J].

ARHART, RJ ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) :5003-&

[2]

Baldwin J E, 1976, J CHEM SOC CHEM COMM, V734

[3] PdCl2-catalyzed reduction of organic halides by triethylsilane [J].

Boukherroub, R ;

Chatgilialoglu, C ;

Manuel, G .

ORGANOMETALLICS, 1996, 15 (05) :1508-1510

[4] NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].

EVANS, DA ;

URPI, F ;

SOMERS, TC ;

CLARK, JS ;

BILODEAU, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216

[5] Stereloselective cascade reactions that incorporate a 7-exo acyl radical cyclization [J].

Grant, SW ;

Zhu, KD ;

Zhang, Y ;

Castle, SL .

ORGANIC LETTERS, 2006, 8 (09) :1867-1870

[6] Palladium-catalyzed hydroarylation of propiolamides. A regio- and stereocontrolled method for preparing 3,3-diarylacrylamides [J].

Hay, LA ;

Koenig, TM ;

Ginah, FO ;

Copp, JD ;

Mitchell, D .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5050-5058

[7] ASYMMETRIC SYNTHESES VIA ENANTIOTOPICALLY SELECTIVE HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDATIONS OF DIOLS CONTAINING A PROCHIRAL CENTER [J].

IRWIN, AJ ;

JONES, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :556-561

[8] Lycopladines B-D and lyconadin B, new alkaloids from Lycopodium complanatum [J].

Ishiuchi, Kan'ichiro ;

Kubota, Takaaki ;

Hoshino, Tomohiro ;

Obara, Yutaro ;

Nakahata, Norimichi ;

Kobayashi, Jun'ichi .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (17) :5995-6000

[9] Lyconadin A, a novel alkaloid from Lycopodium complanatum [J].

Kobayashi, J ;

Hirasawa, Y ;

Yoshida, N ;

Morita, H .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5901-5904

[10] Selective one-pot conversion of carboxylic acids into alcohols [J].

Kokotos, G ;

Noula, C .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :6994-6996