Total Synthesis and Absolute Stereochemistry of Seragakinone A

被引：49

作者：

Takada, Akiomi ^{[1
]}

Hashimoto, Yoshimitsu ^{[1
]}

Takikawa, Hiroshi ^{[1
]}

Hikita, Katsuyoshi ^{[1
]}

Suzuki, Keisuke ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 10期

关键词：

antibiotics; cyclization; natural products; organocatalysis; total synthesis; AROMATIC NITRILE OXIDES; PROMOTED CYCLOCONDENSATION; ASYMMETRIC EPOXIDATION; HYPERVALENT IODINE; ISOXAZOLES; CONVERSION; CONSTRUCTION; OXIDATION; ALDEHYDES;

D O I：

10.1002/anie.201006528

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Cyclic transformation: The key transformations of the asymmetric total synthesis of the marine-derived natural product seragakinone A are two N-heterocyclic carbene catalyzed benzoin cyclizations that result in the construction of two rings and a pinacol-type rearrangement to install the angular prenyl substituent. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2297 / 2301

页数：5

共 47 条

[1]

BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857

[2] Facile construction and divergent transformation of polycyclic isoxazoles: Direct access to polyketide architectures [J].

Bode, JW ;

Hachisu, Y ;

Matsuura, T ;

Suzuki, K .

ORGANIC LETTERS, 2003, 5 (04) :391-394

[3] Amine-promoted cyclocondensation of highly substituted aromatic nitrile oxides with diketones [J].

Bode, JW ;

Hachisu, Y ;

Matsuura, T ;

Suzuki, K .

TETRAHEDRON LETTERS, 2003, 44 (17) :3555-3558

[4]

DALCONTRES GS, 1950, GAZZ CHIM ITAL, V80, P441

[5] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[6] REACTIONS OF SOME SUBSTITUTED ISOXAZOLES WITH ORGANOLITHIUM REAGENTS [J].

GAINER, J ;

HOWARTH, GA ;

HOYLE, W ;

ROBERTS, SM ;

SUSCHITZKY, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (09) :994-997

[7] PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].

GRIFFITH, WP ;

LEY, SV ;

WHITCOMBE, GP ;

WHITE, AD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627

[8] Thiazolium ylide-catalyzed intramolecular aldehyde-ketone benzoin-forming reactions: Substrate scope [J].

Hachisu, Y ;

Bode, JW ;

Suzuki, K .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1097-1100

[9] Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones [J].

Hachisu, Y ;

Bode, JW ;

Suzuki, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (28) :8432-8433

[10] Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography [J].

Ito, Y .

JOURNAL OF CHROMATOGRAPHY A, 2005, 1065 (02) :145-168

← 1 2 3 4 5 →