Synthesis of Spongidine A and D and Petrosaspongiolide L Methyl Ester Using Pyridine C-H Functionalization

被引:10
作者
Bartels, Florian [1 ]
Weber, Manuela [2 ]
Christmann, Mathias [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, Takustr 3, D-14195 Berlin, Germany
[2] Free Univ Berlin, Inst Chem & Biochem, Fabeckstr 34-36, D-14195 Berlin, Germany
关键词
FREE-RADICAL REACTIONS; MARINE SPONGE; BULI-ME2N(CH2)(2)OLI; CONSTRUCTION; ALKYLATION; LITHIATION; ALCOHOLS; OLEFINS; ACCESS; FE;
D O I
10.1021/acs.orglett.9b04315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient strategy for the synthesis of the potent phospholipase A(2) inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer initiated Minisci reaction. A divergent late-stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.
引用
收藏
页码:552 / 555
页数:4
相关论文
共 39 条
[1]  
[Anonymous], THESIS
[2]   Bioinspired synthesis of pentacyclic onocerane triterpenoids [J].
Bartels, Florian ;
Hong, Young J. ;
Ueda, Daijiro ;
Weber, Manuela ;
Sato, Tsutomu ;
Tantillo, Dean J. ;
Christmann, Mathias .
CHEMICAL SCIENCE, 2017, 8 (12) :8285-8290
[3]   Synthesis of three marine natural sesterterpenolides from methyl isoanticopalate.: First enantioselective synthesis of luffolide [J].
Basabe, P ;
Delgado, S ;
Marcos, IS ;
Diez, D ;
Diego, A ;
De Román, M ;
Urones, JG .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9480-9485
[4]   Synthesis of spongidines A and D: marine metabolites phospholipase A2 inhibitors [J].
Basabe, P. ;
Blanco, A. ;
Marcos, I. S. ;
Diez, D. ;
Bodero, O. ;
Martin, M. ;
Urones, J. G. .
TETRAHEDRON, 2011, 67 (20) :3649-3658
[5]  
Blanco-Martin A, 2011, THESIS
[6]   Hydropyridylation of Olefins by Intramolecular Minisci Reaction [J].
Bordi, Samuele ;
Starr, Jeremy T. .
ORGANIC LETTERS, 2017, 19 (09) :2290-2293
[7]   Unusual C-6 lithiation of 2-chloropyridine-mediated by BuLi-Me2N(CH2)2OLi.: New access to 6-functional-2-chloropyridines and chloro-bis-heterocycles [J].
Choppin, S ;
Gros, P ;
Fort, Y .
ORGANIC LETTERS, 2000, 2 (06) :803-805
[8]   Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins [J].
Crossley, Steven W. M. ;
Obradors, Carla ;
Martinez, Ruben M. ;
Shenvi, Ryan A. .
CHEMICAL REVIEWS, 2016, 116 (15) :8912-9000
[9]   Simple, Chemoselective, Catalytic Olefin Isomerization [J].
Crossley, Steven W. M. ;
Barabe, Francis ;
Shenvi, Ryan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (48) :16788-16791
[10]   New pyridinium alkaloids from a marine sponge of the genus Spongia with human phospholipase A2 inhibitor profile [J].
De Marino, S ;
Iorizzi, M ;
Zollo, F ;
Debitus, C ;
Menou, JL ;
Ospina, LF ;
Alcaraz, MJ ;
Payá, M .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (03) :322-326