Total Synthesis of (+)-Gregatin B and E

被引：24

作者：

Kusakabe, Taichi ^{[1
]}

Kawai, Yasuko ^{[1
]}

Kato, Keisuke ^{[1
]}

机构：

[1] Toho Univ, Fac Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 19期

关键词：

PD(II)-MEDIATED CYCLIZATION-CARBONYLATION; COUPLING REACTIONS; IODIDES; ASPERTETRONIN; DERIVATIVES; GREGATINS; REVISIONS; GRAMININ; ALKYNES; ACCESS;

D O I：

10.1021/ol402472q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+)-gregatin E and a new total synthesis of (+)-gregatin B are described. Key features of our synthetic approach involve a palladium-catalyzed cyclization-methoxycarbonylation of optically active propargylic acetate and a Suzuki-Miyaura coupling or CuTC-mediated coupling reaction. The absolute configuration of (+)-gregatin E (5R,5'S) is proposed.

引用

页码：5102 / 5105

页数：4

共 25 条

[1] THE HYDROALUMINATION OF OMEGA-TERBUTOXY ALKYNES - AN EASY ACCESS TO OMEGA-HYDROXY ALKENYL IODIDES - APPLICATION TO THE SYNTHESIS OF DIENIC INSECT PHEROMONES [J].

ALEXAKIS, A ;

DUFFAULT, JM .

TETRAHEDRON LETTERS, 1988, 29 (48) :6243-6246

[2] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].

Allred, GD ;

Liebeskind, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749

[3] An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives [J].

Avenoza, A ;

Cativiela, C ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2001, 12 (09) :1383-1388

[4] ASPERTETRONIN A AND B 2 NOVEL TETRONIC ACID DERIVATIVES PRODUCED BY A BLOCKED MUTANT OF ASPERGILLUS RUGULOSUS [J].

BALLANTINE, JA ;

FERRITO, V ;

HASSALL, CH ;

JONES, VIP .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (01) :56-+

[5] Total Syntheses of the Gregatins A-D and Aspertetronin A: Structure Revisions of These Compounds and of Aspertetronin B, Together with Plausible Structure Revisions of Gregatin E, Cyclogregatin, Graminin A, the Penicilliols A and B, and the Huaspenones A and B [J].

Burghart-Stoll, Heike ;

Brueckner, Reinhard .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (21) :3978-4017

[6] A Serendipitous Synthesis of (+)-Gregatin B, Second Structure Revisions of the Aspertetronins, Gregatins, and Graminin A, Structure Revision of the Penicilliols [J].

Burghart-Stoll, Heike ;

Brueckner, Reinhard .

ORGANIC LETTERS, 2011, 13 (10) :2730-2733

[7] Asymmetric Dihydroxylations of Enynes with a Trisubstituted C=C Bond. An Unprecedented Route to γ-Lactone Building Blocks with a Quaternary Stereocenter [J].

Burghart-Stoll, Heike ;

Kapferer, Tobias ;

Brueckner, Reinhard .

ORGANIC LETTERS, 2011, 13 (05) :1016-1019

[8] The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes:: Synthesis of (E)-1-tributylstannyl-1-alkenes [J].

Darwish, Alla ;

Lang, Adam ;

Kim, Thomas ;

Chong, J. Michael .

ORGANIC LETTERS, 2008, 10 (05) :861-864

[9] Synthesis of E-vinyl iodides via Pd-catalyzed hydrostannation of terminal alkynes [J].

Darwish, Alla ;

Chong, J. Michael .

TETRAHEDRON, 2012, 68 (02) :654-658

[10] Characterization of DMSO Coordination to Palladium(II) in Solution and Insights into the Aerobic Oxidation Catalyst, Pd(DMSO)2(TFA)2 [J].

Diao, Tianning ;

White, Paul ;

Guzei, Ilia ;

Stahl, Shannon S. .

INORGANIC CHEMISTRY, 2012, 51 (21) :11898-11909

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