A concise asymmetric synthesis of (-)-rasfonin

被引：22

作者：

Huang, Yange ^{[1
]}

Minnaard, Adriaan J. ^{[1
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 01期

关键词：

CONTAINING NATURAL-PRODUCT; ABSOLUTE STEREOCHEMISTRY; CONJUGATE ADDITION; TT-1; RASFONIN; RAS; ACID; LOCALIZATION; EFFICIENT; SUBUNITS; FUNGUS;

D O I：

10.1039/c1ob06700a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very efficient total synthesis of the apoptosis inducer (-)-rasfonin has been developed using CuBr/JosiPhos catalyzed iterative asymmetric conjugate addition of MeMgBr and Feringa's butenolide.

引用

页码：29 / 31

页数：3

共 31 条

[1] Total synthesis of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus Trichurus terrophilus [J].

Akiyama, K ;

Yamamoto, S ;

Fujimoto, H ;

Ishibashi, M .

TETRAHEDRON, 2005, 61 (07) :1827-1833

[2] Absolute stereochemistry of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus, Trichurus terrophilus [J].

Akiyama, K ;

Kawamoto, S ;

Fujimoto, H ;

Ishibashi, M .

TETRAHEDRON LETTERS, 2003, 44 (46) :8427-8431

[3] Toward the development of a general chiral auxiliary. Enantioselective alkylation and a new catalytic asymmetric addition of silyloxyfurans: Application to a total synthesis of (-)-rasfonin [J].

Boeckman, Robert K., Jr. ;

Pero, Joseph E. ;

Boehmler, Debra J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11032-11033

[4] Lipidated Ras and Rab peptides and proteins - Synthesis, structure, and function [J].

Brunsveld, Luc ;

Kuhlmann, Juergen ;

Alexandrov, Kirill ;

Wittinghofer, Alfred ;

Goody, Roger S. ;

Waldmann, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6622-6646

[5] Small-molecule inhibition of APT1 affects Ras localization and signaling [J].

Dekker, Frank J. ;

Rocks, Oliver ;

Vartak, Nachiket ;

Menninger, Sascha ;

Hedberg, Christian ;

Balamurugan, Rengarajan ;

Wetzel, Stefan ;

Renner, Steffen ;

Gerauer, Marc ;

Schoelermann, Beate ;

Rusch, Marion ;

Kramer, John W. ;

Rauh, Daniel ;

Coates, Geoffrey W. ;

Brunsveld, Luc ;

Bastiaens, Philippe I. H. ;

Waldmann, Herbert .

NATURE CHEMICAL BIOLOGY, 2010, 6 (06) :449-456

[6] Structure and Absolute Stereochemistry of the Anticancer Agent EBC-23 from the Australian Rainforest [J].

Dong, Lin ;

Gordon, Victoria A. ;

Grange, Rebecca L. ;

Johns, Jenny ;

Parsons, Peter G. ;

Porzelle, Achim ;

Reddell, Paul ;

Schill, Heiko ;

Williams, Craig M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (46) :15262-+

[7] Stereoselective Synthesis of (+)-Goniodiol, (+)-Goniotriol, (-)-Goniofupyrone, and (+)-Altholactone Using a Catalytic Asymmetric Hetero-Diels-Alder/Allylboration Approach [J].

Favre, Annaick ;

Carreaux, Francois ;

Deligny, Michael ;

Carboni, Bertrand .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) :4900-4907

[8] SYNTHESIS OF ENANTIOMERICALLY PURE GAMMA-(MENTHYLOXY)BUTENOLIDES AND (R)-2-METHYL-1,4-BUTANEDIOL AND (S)-2-METHYL-1,4-BUTANEDIOL [J].

FERINGA, BL ;

DELANGE, B ;

DEJONG, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2471-2475

[9] Total syntheses of ipomoeassin B and E [J].

Fuerstner, Alois ;

Nagano, Takashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1906-+

[10]

FUJIMOTO H, 2000, 120 ANN M PHARM SOC, P68

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