Enzymatically Asymmetrised Chiral Building Blocks for the Synthesis of Complex Natural Product Analogues: The Synthesis of Dynemicin Analogues from 2-(Quinolin-4-yl)propane-1,3-diol

被引:3
作者
Riva, Renata [1 ]
Banfi, Luca [1 ]
Basso, Andrea [1 ]
Gandolfo, Valentina [1 ]
Guanti, Giuseppe [1 ]
机构
[1] Univ Genoa, Dept Chem & Ind Chem, I-16146 Genoa, Italy
关键词
Antitumor agents; Diastereoselectivity; Nitrogen heterocycles; Alkynes; Enediynes; ANTITUMOR-ACTIVITY; BIOLOGICAL EVALUATION; GLYCEROL DERIVATIVES; ENEDIYNES; CHEMISTRY; LIPASE; DESIGN; ACID; UNCIALAMYCIN; ENANTIOMERS;
D O I
10.1002/ejoc.200901478
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Full details of our synthetic approaches directed towards the enantioselective synthesis of new dynemicin analogues each containing a side-arm (a "handle") incorporating a protected alcohol are reported.
引用
收藏
页码:2768 / 2787
页数:20
相关论文
共 69 条
[1]   ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].
ADER, U ;
BREITGOFF, D ;
KLEIN, P ;
LAUMEN, KE ;
SCHNEIDER, MP .
TETRAHEDRON LETTERS, 1989, 30 (14) :1793-1796
[2]   Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle [J].
Banfi, L ;
Basso, A ;
Gandolfo, V ;
Guanti, G ;
Riva, R .
TETRAHEDRON LETTERS, 2004, 45 (22) :4221-4223
[3]   Lipase catalyzed asymmetrization of quinolyl substituted 1,3-propanediols [J].
Banfi, L ;
Guanti, G ;
Mugnoli, A ;
Riva, R .
TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2481-2492
[4]   Rational design, synthesis, and reactivity of lactendiynes, a new class of cyclic enediynes ortho-fused with the beta-lactam ring [J].
Banfi, L ;
Basso, A ;
Guanti, G .
TETRAHEDRON, 1997, 53 (09) :3249-3268
[5]   Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties [J].
Banfi, Luca ;
Basso, Andrea ;
Bevilacqua, Elisabetta ;
Gandolfo, Valentina ;
Giannini, Giuseppe ;
Guanti, Giuseppe ;
Musso, Loana ;
Paravidino, Monica ;
Riva, Renata .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) :3501-3518
[6]   Synthetic approaches towards a new class of strained "lactenediynes" [J].
Banfi, Luca ;
Basso, Andrea ;
Guanti, Giuseppe ;
Paravidino, Monica ;
Riva, Renata ;
Scapolla, Carlo .
ARKIVOC, 2006, :15-39
[7]   ASYMMETRIC-SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 5,10-DIDEAZA-5,6,7,8-TETRAHYDROPTEROIC ACID AND 5,10-DIDEAZA-5,6,7,8-TETRAHYDROFOLIC ACID (DDATHF) [J].
BARNETT, CJ ;
WILSON, TM .
TETRAHEDRON LETTERS, 1989, 30 (46) :6291-6294
[8]   Total synthesis of (+)-papuamine: An antifungal pentacyclic alkaloid from a marine sponge, Haliclona sp. [J].
Barrett, AGM ;
Boys, ML ;
Boehm, TL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :685-699
[9]  
BESTMANN HJ, 1980, LIEBIGS ANN CHEM, P2061
[10]   ENANTIOSELECTIVE SYNTHESES AND ABSOLUTE-CONFIGURATIONS OF VIRIDIENE AND AUCANTENE, 2 CONSTITUENTS OF ALGAE PHEROMONE BOUQUETS [J].
BOLAND, W ;
NIEDERMEYER, U ;
JAENICKE, L .
HELVETICA CHIMICA ACTA, 1985, 68 (07) :2062-2073