A CONCISE SYNTHESIS OF SOLAMIN AND CIS-SOLAMIN, MONO-THF ACETOGENINS FROM ANNONA MURICATA

被引:8
作者
Makabe, Hidefumi [1 ,2 ]
Kuwabara, Asuka [1 ]
Hattori, Yasunao [2 ,3 ]
Konno, Hiroyuki [4 ]
机构
[1] Shinshu Univ, Grad Sch Agr, Nagano 3994598, Japan
[2] Shinshu Univ, Interdisciplinary Grad Sch Sci & Technol, Nagano 3994598, Japan
[3] Shinshu Univ, Satellite Venture Business Lab, Nagano 3868567, Japan
[4] Kyoto Prefectural Univ Med, Grad Sch Med Sci, Dept Chem, Kyoto 6038334, Japan
关键词
Acetogenin; Antitumor; Asymmetric Synthesis; Polyketide; THF Ring; MITOCHONDRIAL COMPLEX-I; INHIBITORY-ACTION; OXIDATIVE CYCLIZATION; PYRANICIN; DIASTEREOMERS; RETICULATACIN; ANALOGS;
D O I
10.3987/COM-09-11741
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise total synthesis of solamin (1) and cis-solamin (2) was performed using an epoxy alcohol (11) as a versatile chiral building block for synthesizing the stereoisomers of the mono-THF annonaceous acetogenins.
引用
收藏
页码:2369 / 2376
页数:8
相关论文
共 27 条
[1]   Acetogenins from Annonaceae:: recent progress in isolation, synthesis and mechanisms of action [J].
Bermejo, A ;
Figadère, B ;
Zafra-Polo, MC ;
Barrachina, I ;
Estornell, E ;
Cortes, D .
NATURAL PRODUCT REPORTS, 2005, 22 (02) :269-303
[2]   Total synthesis and preliminary biological evaluation of cis-solamin isomers [J].
Cecil, ARL ;
Hu, YL ;
Vicent, MJ ;
Duncan, R ;
Brown, RCD .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3368-3374
[3]   Synthesis of cis-Solamin using a permanganate-mediated oxidative cyclization [J].
Cecil, ARL ;
Brown, RCD .
ORGANIC LETTERS, 2002, 4 (21) :3715-3718
[4]   Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I [J].
Furuhata, Shin-ichi ;
Hattori, Yasunao ;
Okajima, Motonori ;
Konno, Hiroyuki ;
Abe, Masato ;
Miyoshi, Hideto ;
Goto, Tetsuhisa ;
Makabe, Hidefumi .
TETRAHEDRON, 2008, 64 (33) :7695-7703
[5]   cis-monotetrahydrofuran acetogenins from the roots of Annona muricata [J].
Gleye, C ;
Duret, P ;
Laurens, A ;
Hocquemiller, R ;
Cavé, A .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05) :576-579
[6]   Total synthesis of cis-solamin:: Exploiting the RuO4-catalyzed oxidative cyclization of dienes [J].
Goeksel, Huelya ;
Stark, Christian B. W. .
ORGANIC LETTERS, 2006, 8 (16) :3433-3436
[7]   A Concise and Modular Synthesis of Pyranicin [J].
Griggs, Nolan D. ;
Phillips, Andrew J. .
ORGANIC LETTERS, 2008, 10 (21) :4955-4957
[8]   Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex I [J].
Hattori, Yasunao ;
Furuhata, Shin-ichi ;
Okajima, Motonori ;
Konno, Hiroyuki ;
Abe, Masato ;
Miyoshi, Hideto ;
Goto, Tetsuhisa ;
Makabe, Hidefumi .
ORGANIC LETTERS, 2008, 10 (05) :717-720
[9]   Synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin and their inhibitory action with bovine heart mitochondrial complex I [J].
Hattori, Yasunao ;
Kimura, Yuka ;
Moroda, Aki ;
Konno, Hiroyuki ;
Abe, Masato ;
Miyoshi, Hideto ;
Goto, Tetsuhisa ;
Makabe, Hidefumi .
CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (06) :894-904
[10]   Highly stereoselective and modular syntheses of 10-hydroxytrilobacin and three diastereomers via stereodivergent [3+2]-annulation reactions [J].
Huh, Chan Woo ;
Roush, William R. .
ORGANIC LETTERS, 2008, 10 (15) :3371-3374