Cycloadditions in the Total Synthesis of Sporolide B

被引:21
作者
Li, Pengfei [1 ]
Menche, Dirk [1 ]
机构
[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
biomimetic synthesis; cycloaddition; natural products; selectivity; total synthesis; ACTINOMYCETE SALINISPORA-TROPICA; CATALYZED 2+2+2 CYCLOADDITION; ALKYNE CYCLOTRIMERIZATION; CONSTRUCTION; 1,6-DIYNES; COMPLEXES;
D O I
10.1002/anie.200901894
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Closing rings: A recent total synthesis of sporolide B by the Nicolaou group is highlighted by two advantageous cycloadditions. Firstly, a regioselective [2+2+2] cycloaddition of highly elaborate substrates assembles the halogenated aromatic ring and subsequently an orthoquinone [4+2] cyclization closes stereoselectively the dioxane-containing macrocycle. These approaches should be considered in complex target syntheses. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5078 / 5080
页数:3
相关论文
共 37 条
[1]  
Agenet N., 2007, ORG REACT, V68, P1
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]   Total synthesis of (±)-haouamine A [J].
Baran, PS ;
Burns, NZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3908-3909
[4]   Sporolides A and B:: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica [J].
Buchanan, GO ;
Williams, PG ;
Feling, RH ;
Kauffman, CA ;
Jensen, PR ;
Fenical, W .
ORGANIC LETTERS, 2005, 7 (13) :2731-2734
[5]   [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].
Chopade, Pramod R. ;
Louie, Janis .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327
[6]   Developing a new resource for drug discovery: marine actinomycete bacteria [J].
Fenical, William ;
Jensen, Paul R. .
NATURE CHEMICAL BIOLOGY, 2006, 2 (12) :666-673
[7]  
Galan B. R., 2009, ANGEW CHEM, V121, P2870
[8]   Beyond Reppe: Building Substituted Arenes by [2+2+2] Cycloadditions of Alkynes [J].
Galan, Brandon R. ;
Rovis, Tomislav .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2830-2834
[9]   The fascinating construction of pyridine ring systems by transition metal-catalysed [2+2+2] cycloaddition reactions [J].
Heller, Barbara ;
Hapke, Marko .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1085-1094
[10]   De novo synthesis of substituted pyridines [J].
Henry, GD .
TETRAHEDRON, 2004, 60 (29) :6043-6061