Alkyne Carbonyl Metathesis As a Means To Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone

被引：38

作者：

Nayak, Maloy

Kim, Ikyon ^{[1
]}

机构：

[1] Yonsei Univ, Coll Pharm, Inchon 406840, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 22期

基金：

新加坡国家研究基金会;

关键词：

DEGUELIN; ROTENOIDS; ACID; ALDEHYDES; METHYL; CYCLIZATION; ACETYLENES; STRATEGY; PHENOLS; OXYGEN;

D O I：

10.1021/acs.joc.5b02160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly convergent synthetic approach to rotenoid natural products is described. Successful,pairing of two building blocks,for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready, access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (+/-)-degnelin and (+/-)-munduserone in high overall yields.

引用

收藏

页码：11460 / 11467

页数：8

相关论文

共 60 条

[1] NOVEL AND EFFICIENT SYNTHESIS OF ROTENOIDS VIA INTRAMOLECULAR RADICAL ARYLATION [J].

AHMADJUNAN, SA ;

AMOS, PC ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :539-545

[2] ROTENOID INTERCONVERSION - SYNTHESIS OF DEGUELIN FROM ROTENONE [J].

ANZEVENO, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2578-2580

[3] Multidimensional optimization of promising antitumor xanthone derivatives [J].

Azevedo, Carlos M. G. ;

Afonso, Carlos M. M. ;

Sousa, Diana ;

Lima, Raquel T. ;

Helena Vasconcelos, M. ;

Pedro, Madalena ;

Barbosa, Joao ;

Correa, Arlene G. ;

Reis, Salette ;

Pinto, Madalena M. M. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (11) :2941-2959

[4] NOVEL METHODS FOR SYNTHESIS OF 2-2-DIMETHYLCHROMENS [J].

BANDARANAYAKE, WM ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (17) :970-+

[5] PYRIDINE-CATALYSED CHROMENYLATION OF MONO-CHELATED META-DIHYDRIC PHENOLS WITH MONO-TERPENE, SESQUI-TERPENE AND DI-TERPENE ALDEHYDES - SYNTHESIS OF RUBRANINE AND FLEMINGINS-A-METHYL, FLEMINGINS-B-METHYL AND FLEMINIGINS-C-METHYL ETHERS [J].

BANDARANAYAKE, WM ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (04) :804-+

[6] Highly Variable Insect Control Efficacy of Tephrosia vogelii Chemotypes [J].

Belmain, Steven R. ;

Amoah, Barbara A. ;

Nyirenda, Stephen P. ;

Kamanula, John F. ;

Stevenson, Philip C. .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (40) :10055-10063

[7] FeCl3-catalyzed synthesis of functionally diverse dibenzo[b,f]oxepines and benzo[b]oxepines via alkyne-aldehyde metathesis [J].

Bera, Krishnendu ;

Jalal, Swapnadeep ;

Sarkar, Soumen ;

Jana, Umasish .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) :57-61

[8] Prenylated Isoflavonoids: Botanical Distribution, Structures, Biological Activities and Biotechnological Studies. An Update (1995-2006) [J].

Botta, Bruno ;

Menendez, Pilar ;

Zappia, Giovanni ;

de Lima, Roberto Alves ;

Torge, Roberta ;

Delle Monache, Giuliano .

CURRENT MEDICINAL CHEMISTRY, 2009, 16 (26) :3414-3468

[9]

Bueno Perez L., 2014, ORG LETT, V16, P1462

[10] REGIOSELECTIVE ETHER CLEAVAGES OF ROTENOIDS - SPIRO-ETHER FORMATION AND STEREOSELECTIVE ISOTOPIC LABELING OF (E)-PRENYL OR (Z)-PRENYL METHYL-GROUPS IN (6AS, 12AS)-ROT-2'-ENONIC ACID [J].

CARSON, D ;

CROMBIE, L ;

KILBEE, GW ;

MOFFATT, F ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03) :779-788

← 1 2 3 4 5 6 →