Total Synthesis of A Novel Tetracyclic Alkaloid, Cassiarin F from the Flowers of Cassia siamea

被引:19
作者
Deguchi, Jun [1 ]
Hirahara, Tomoe [1 ]
Oshimi, Shiori [1 ]
Hirasawa, Yusuke [1 ]
Ekasari, Wiwied [2 ]
Shirota, Osamu [3 ]
Honda, Toshio [1 ]
Morita, Hiroshi [1 ]
机构
[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan
[2] Airlangga Univ, Fac Pharm, Jalan Dharmawangsa Dalam 60286, Surabaya, Indonesia
[3] Tokushima Bunri Univ, Kagawa Campus, Fac Pharmaceut Sci, Sanuki City, Kagawa 7692193, Japan
关键词
VITRO ANTIPLASMODIAL ACTIVITY; HOUBEN-HOESCH; TRADITIONAL MEDICINE; INVOLVEMENT; GATTERMANN;
D O I
10.1021/ol201674a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel alkaloid, cassiarin F (1), which showed potent antiplasmodial activity against Plasmodium falciparum In vitro, was isolated from the flowers of Cassia siamea, and Its structure was elucidated on the basis of 2D NMR analyses. A total synthesis of 1 was also achieved by employing the Suzuki coupling constructing biaryl unit, nucleophilic aromatic substitution, and Houben-Hoesch type ring construction as key steps.
引用
收藏
页码:4344 / 4347
页数:4
相关论文
共 18 条
[1]   THE CHEMISTRY OF NITRILIUM SALTS .3. THE IMPORTANCE OF TRIAZINIUM SALTS IN HOUBEN-HOESCH REACTIONS CATALYZED BY TRIFLUOROMETHANESULFONIC ACID [J].
AMER, MI ;
BOOTH, BL ;
NOORI, GFM ;
PROENCA, MFJRP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (05) :1075-1082
[2]   NITRILE OXIDE-BF3 COMPLEX AS ELECTROPHILIC MOIETY TOWARDS AROMATIC SYSTEMS - STEREOSPECIFIC SYNTHESIS OF OXIMES [J].
AURICCHIO, S ;
BINI, A ;
PASTORMERLO, E ;
RICCA, A ;
TRUSCELLO, AM .
TETRAHEDRON, 1994, 50 (25) :7589-7596
[3]   Ancisheynine, the first N,C-coupled naphthylisoquinoline alkaloid:: Total synthesis and stereochemical analysis [J].
Bringmann, G ;
Guider, T ;
Reichert, M ;
Meyer, F .
ORGANIC LETTERS, 2006, 8 (06) :1037-1040
[4]   SYNTHESIS OF AZAANTHRAQUINONES - HOMOLYTIC SUBSTITUTION OF PYRIDINES [J].
CAMERON, DW ;
DEUTSCHER, KR ;
FEUTRILL, GI ;
HUNT, DE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (07) :1451-1468
[5]   ANTIMALARIAL ACTIVITY OF CASSIARIN A FROM THE LEAVES OF CASSIA SIAMEA [J].
Ekasari, Wiwied ;
Widyawaruyanti, Aty ;
Zaini, Noor Cholies ;
Syafruddin, Din ;
Honda, Toshio ;
Morita, Hiroshi .
HETEROCYCLES, 2009, 78 (07) :1831-1836
[6]   Synthesis of RHPS4 via an anionic ring closing cascade [J].
Kristensen, Jesper Langgaard .
TETRAHEDRON LETTERS, 2008, 49 (15) :2351-2354
[7]   In vitro antiplasmodial activity of 18 plants used in Congo Brazzaville traditional medicine [J].
Mbatchi, SF ;
Mbatchi, B ;
Banzouzi, JT ;
Bansimba, T ;
Ntandou, GFN ;
Ouamba, JM ;
Berry, A ;
Benoit-Vical, F .
JOURNAL OF ETHNOPHARMACOLOGY, 2006, 104 (1-2) :168-174
[8]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[9]   Cassiarins A and B, novel antiplasmodial alkaloids from Cassia siamea [J].
Morita, Hiroshi ;
Oshimi, Shiori ;
Hirasawa, Yusuke ;
Koyama, Koichiro ;
Honda, Toshio ;
Ekasari, Wiwied ;
Indrayanto, Gunawan ;
Zaini, Noor Cholies .
ORGANIC LETTERS, 2007, 9 (18) :3691-3693
[10]   Synthesis and structure-activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity [J].
Morita, Hiroshi ;
Tomizawa, Yuichiro ;
Deguchi, Jun ;
Ishikawa, Tokio ;
Arai, Hiroko ;
Zaima, Kazumasa ;
Hosoya, Takahiro ;
Hirasawa, Yusuke ;
Matsumoto, Takayuki ;
Kamata, Katsuo ;
Ekasari, Wiwied ;
Widyawaruyanti, Aty ;
Wahyuni, Tutik Sri ;
Zaini, Noor Cholies ;
Honda, Toshio .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (24) :8234-8240