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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 02期

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

页码：552 / 555

页数：4

共 39 条

[11] Westphal reaction in solid-phase [J].

Delgado, F ;

Linares, ML ;

Alajarín, R ;

Vaquero, JJ ;

Alvarez-Builla, J .

ORGANIC LETTERS, 2003, 5 (22) :4057-4060

[12] Phospholipase A2 Enzymes: Physical Structure, Biological Function, Disease Implication, Chemical Inhibition, and Therapeutic Intervention [J].

Dennis, Edward A. ;

Cao, Jian ;

Hsu, Yuan-Hao ;

Magrioti, Victoria ;

Kokotos, George .

CHEMICAL REVIEWS, 2011, 111 (10) :6130-6185

[13] Minisci reactions: Versatile CH-functionalizations for medicinal chemists [J].

Duncton, Matthew A. J. .

MEDCHEMCOMM, 2011, 2 (12) :1135-1161

[14] Attempted synthesis of spongidines by a radical cascade terminating onto a pyridine ring [J].

Gonzalez, Miguel A. ;

Molina-Navarro, Sonia .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7462-7465

[15] Aggregative activation in heterocyclic chemistry .4. Metallation of 2-methoxypyridine: unusual behaviour of the new unimetal superbase BuLi-Me2N(CH2)(2)OLi (BuLi-LiDMAE) [J].

Gros, P ;

Fort, Y ;

Caubere, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (20) :3071-3080

[16] SELECTIVE CATALYTIC OXYDATIONS BY MEANS OF NOBLE METAL CATALYSTS [J].

HEYNS, K ;

PAULSEN, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1957, 69 (18-9) :600-608

[17] Selective Functionalization of Pyridines via Heterocyclic Phosphonium Salts [J].

Hilton, Michael C. ;

Dolewski, Ryan D. ;

McNally, Andrew .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (42) :13806-13809

[18] Total Synthesis of Viridin and Viridiol [J].

Ji, Yang ;

Xin, Zhengyuan ;

He, Haibing ;

Gao, Shuanhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (41) :16208-16212

[19] N-OXIDES AND RELATED-COMPOUNDS .60. NOVEL THERMAL AND PHOTOCHEMICAL REARRANGEMENTS OF N-SUBSTITUTED 2-PYRIDONES [J].

KATRITZKY, AR ;

CHAPMAN, AV ;

COOK, MJ ;

MILLET, GH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2743-2754

[20] A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids [J].

Kinzel, Tom ;

Zhang, Yong ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14073-14075

← 1 2 3 4 →