Concise Asymmetric Synthesis of (+)-Conocarpan and Obtusafuran

被引：22

作者：

Chen, Cheng-yi ^{[1
]}

Weisel, Mark ^{[1
]}

机构：

[1] Merck Res Labs, Rahway, NJ 07065 USA

来源：

SYNLETT | 2013年 / 24卷 / 02期

关键词：

(+)-conocarpan; (+)- and (-)-obtusafuran; dynamic kinetic resolution; SNAr reaction; metal-catalyzed C-O bond formation; trans-dihydrobenzofuran; 8,5 '-neolignans; 8-aryl-2,3-dihydro-benzofuran; NEOLIGNANS;

D O I：

10.1055/s-0032-1317704

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of three natural products: (+)-conocarpan, both (+)- and (-)-obtusafuran is disclosed. The highlights of the synthesis are the enantioselective hydrogenation of prochiral ketones via dynamic kinetic resolution to afford chiral alcohols. Intramolecular ring closure via either SNAr reaction or metal-catalyzed C-O bond formation led to the construction of the trans-dihydrobenzofuran core.

引用

收藏

页码：189 / 192

页数：4

相关论文

共 25 条

[1] Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings:: A convergent synthesis of diverse benzofuran neolignans [J].

Akai, S ;

Morita, N ;

Iio, K ;

Nakamura, Y ;

Kita, Y .

ORGANIC LETTERS, 2000, 2 (15) :2279-2282

[2] Flavonoids from the Heartwood of Dalbergia odorifera and Their Protective Effect on Glutamate-Induced Oxidative Injury in HT22 Cells [J].

An, Ren-Bo ;

Jeong, Gil-Saeng ;

Kim, Youn-Chul .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (12) :1722-1724

[3] Lignans and neolignans as lead compounds [J].

S. Apers ;

A. Vlietinck ;

L. Pieters .

Phytochemistry Reviews, 2003, 2 (3) :201-217

[4] Lignan Derivatives from Krameria lappacea Roots Inhibit Acute Inflammation in Vivo and Pro-inflammatory Mediators in Vitro [J].

Baumgartner, Lisa ;

Sosa, Silvio ;

Atanasov, Atanas G. ;

Bodensieck, Antje ;

Fakhrudin, Nanang ;

Bauer, Julia ;

Del Favero, Giorgia ;

Ponti, Cristina ;

Heiss, Elke H. ;

Schwaiger, Stefan ;

Ladurner, Angela ;

Widowitz, Ute ;

Della Loggia, Roberto ;

Rollinger, Judith M. ;

Werz, Oliver ;

Bauer, Rudolf ;

Dirsch, Verena M. ;

Tubaro, Aurelia ;

Stuppner, Hermann .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (08) :1779-1786

[5] Insecticidal neolignans from Piper decurrens [J].

Chauret, DC ;

Bernard, CB ;

Arnason, JT ;

Durst, T ;

Krishnamurty, HG ;

SanchezVindas, P ;

Moreno, N ;

SanRoman, L ;

Poveda, L .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (02) :152-155

[6] Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity [J].

Chen, Cheng-yi ;

Frey, Lisa F. ;

Shultz, Scott ;

Wallace, Debra J. ;

Marcantonio, Karen ;

Payack, Joeseph F. ;

Vazquez, Enrique ;

Springfield, Shawn A. ;

Zhou, George ;

Liu, Ping ;

Kieczykowski, Gerard R. ;

Chen, Alex M. ;

Phenix, Brian D. ;

Singh, Utpal ;

Strine, Jeff ;

Izzo, Brianne ;

Krska, Shane W. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :616-623

[7] Antitrypanosomal activity of a novel norlignan purified from Nectandra lineata [J].

Chérigo, L ;

Polanco, V ;

Ortega-Barria, E ;

Heller, MV ;

Capson, TL ;

Rios, LC .

NATURAL PRODUCT RESEARCH, 2005, 19 (04) :373-377

[8] Diastereoselective Friedel-Crafts alkylation of indoles with chiral (α-phenyl benzylic cations.: Asymmetric synthesis of anti-1,1,2-triarylalkanes [J].

Chung, John Y. L. ;

Mancheno, Danny ;

Dormer, Peter G. ;

Variankaval, Narayan ;

Ball, Richard G. ;

Tsou, Nancy N. .

ORGANIC LETTERS, 2008, 10 (14) :3037-3040

[9] Synthesis of (-)-conocarpan by two routes based on radical cyclization and establishment of its absolute configuration [J].

Clive, Derrick L. J. ;

Stoffman, Elia J. L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (10) :1831-1842

[10] One-Pot, Pd-Catalyzed Synthesis of trans-Dihydrobenzofurans from o-Aminophenols [J].

Coy B, Ericsson D. ;

Jovanovic, Ljubisa ;

Sefkow, Michael .

ORGANIC LETTERS, 2010, 12 (09) :1976-1979