Synthetic Studies on Spirolides A and B: Formation of the Upper Carbon Framework Based on a Lewis Acid Template-Catalyzed Diels-Alder Reaction

被引：6

作者：

Ishihara, Jun ^{[1
]}

Usui, Fuma ^{[1
]}

Kurose, Tomohiro ^{[1
]}

Baba, Tomohiro ^{[1
]}

Kawaguchi, Yasunori ^{[1
]}

Watanabe, Yuki ^{[1
]}

Hatakeyama, Susumi ^{[2
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan

[2] Nagasaki Univ, Med Innovat Ctr, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 06期

基金：

日本学术振兴会;

关键词：

catalytic reaction; Diels-Alder reaction; Lewis acids; natural products; spiro compounds; stereoselective reactions; DINOFLAGELLATE ALEXANDRIUM-OSTENFELDII; MARINE TOXIN; STEREOSELECTIVE CONSTRUCTION; RELATIVE STEREOCHEMISTRY; STRUCTURAL DETERMINANTS; BIOLOGICAL EVALUATION; SECONDARY ALCOHOLS; CARBOXYLIC-ACIDS; SHELLFISH POISON; ABYSSOMICIN-C;

D O I：

10.1002/chem.201804977

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The upper fragment of spirolides A and B, which are marine phycotoxins that exhibit strong antagonistic activities on nicotinic acetylcholine receptors, was constructed. The functionalized cyclohexene in spirolides was stereoselectively synthesized from the bicyclic lactone, which could be readily accessed by the Lewis acid template-catalyzed asymmetric Diels-Alder reaction of the pentadienol and methyl acrylate.

引用

收藏

页码：1543 / 1552

页数：10

相关论文

共 81 条

[1] Detection and identification of spirolides in Norwegian shellfish and plankton [J].

Aasen, J ;

MacKinnon, SL ;

LeBlanc, P ;

Walter, JA ;

Hovgaard, P ;

Aune, T ;

Quilliam, MA .

CHEMICAL RESEARCH IN TOXICOLOGY, 2005, 18 (03) :509-515

[2]

Amzil Z, 2007, MAR DRUGS, V5, P168, DOI 10.3390/md20070013

[3]

[Anonymous], ANGEW CHEM

[4] Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A [J].

Araoz, Romulo ;

Servent, Denis ;

Molgo, Jordi ;

Iorga, Bogdan I. ;

Fruchart-Gaillard, Carole ;

Benoit, Evelyne ;

Gu, Zhenhua ;

Stivala, Craig ;

Zakarian, Armen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10499-10511

[5] Partially hydrogenated 1,1′-binaphthyl as ligand scaffold in metal-catalyzed asymmetric synthesis [J].

Au-Yeung, TTL ;

Chan, SS ;

Chan, ASC .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (05) :537-555

[6] (BDP)CuH: A "hot" Stryker's reagent for use in achiral conjugate reductions [J].

Baker, Benjamin A. ;

Bokovic, Zarko V. ;

Lipshutz, Bruce H. .

ORGANIC LETTERS, 2008, 10 (02) :289-292

[7] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[8]

Beaumont S, 2010, EUR J ORG CHEM, V2010, P5743, DOI [10.1002/e.joc.201000842, 10.1002/ejoc.201000842]

[9] Marine Macrocyclic Imines, Pinnatoxins A and G: Structural Determinants and Functional Properties to Distinguish Neuronal α7 from Muscle α12βγδ nAChRs [J].

Bourne, Yves ;

Sulzenbacher, Gerlind ;

Radic, Zoran ;

Araoz, Romulo ;

Reynaud, Morgane ;

Benoit, Evelyne ;

Zakarian, Armen ;

Servent, Denis ;

Molgo, Jordi ;

Taylor, Palmer ;

Marchot, Pascale .

STRUCTURE, 2015, 23 (06) :1106-1115

[10] Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism [J].

Bourne, Yves ;

Radic, Zoran ;

Araoz, Romulo ;

Talley, Todd T. ;

Benoit, Evelyne ;

Servent, Denis ;

Taylor, Palmer ;

Molgo, Jordi ;

Marchot, Pascale .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (13) :6076-6081

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