Synthesis of (±)-γ-Rubromycin via a New Hypoiodite-Catalytic Oxidative Cycloetherification

被引：26

作者：

Wei, Liping ^{[1
]}

Xue, Jijun ^{[1
]}

Liu, Hongbiao ^{[1
]}

Wang, Wenjing ^{[1
]}

Li, Ying ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 20期

关键词：

ALTERNATIVE SPIROKETALIZATION METHODS; IN-SITU GENERATION; HUMAN TELOMERASE; PURPUROMYCIN; COMBINATORIAL; DERIVATIVES; SPIROLACTONIZATION; DEAROMATIZATION; HELIQUINOMYCIN; RUBROMYCINS;

D O I：

10.1021/ol3024874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of gamma-rubromycin is presented through a new oxidative, bisbenzannulated spiroketalization as a key step which is catalyzed by an in situ generated hypoiodite species, developed previously by our group. This key transformation has high efficiency and convenient conditions. This is a new and efficient catalytic application for organohypoiodine reagents.

引用

页码：5302 / 5305

页数：4

共 43 条

[1] Total synthesis of (±)-γ-Rubromycin on the basis of two aromatic pummerer-type reactions [J].

Akai, Shuji ;

Kakiguchi, Keisuke ;

Nakamura, Yuka ;

Kuriwaki, Ikumi ;

Dohi, Toshifumi ;

Harada, Shusaku ;

Kubo, Ozora ;

Morita, Nobuyoshi ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7458-7461

[2] Alternative Spiroketalization Methods toward Purpuromycin: A Hemiketal Conjugate Addition Strategy and Use of an Electron-Rich Isocoumarin Precursor [J].

Bandichhor, Rakeshwar ;

Lowell, Andrew N. ;

Kozlowski, Marisa C. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) :6475-6487

[3] STRUCTURE DETERMINATION OF PURPUROMYCIN, A NEW ANTIBIOTIC [J].

BARDONE, MR ;

MARTINELLI, E ;

ZERILLI, LF ;

CORONELLI, C .

TETRAHEDRON, 1974, 30 (16) :2747-2754

[4] RUBROMYCINS .3. CONSTITUTION OF ALPHA-RUBROMYCIN, BETA-RUBROMYCIN, GAMMA-RUBROMYCIN, AND GAMMA-ISO-RUBROMYCIN [J].

BROCKMAN.H ;

ZEECK, A .

CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (06) :1709-&

[5]

BROCKMANN H, 1966, TETRAHEDRON LETT, P3525

[6] RUBROMYCINS .2. [J].

BROCKMANN, H ;

LENK, W ;

SCHWANTJE, G ;

ZEECK, A .

CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (01) :126-+

[7] Effect of a novel antibiotic, heliquinomycin, on DNA helicase and cell growth [J].

Chino, M ;

Nishikawa, K ;

Yamada, A ;

Ohsono, M ;

Sawa, T ;

Hanaoka, F ;

Ishizuka, M ;

Takeuchi, T .

JOURNAL OF ANTIBIOTICS, 1998, 51 (05) :480-486

[8] Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant [J].

Dohi, T ;

Maruyama, A ;

Yoshimura, M ;

Morimoto, K ;

Tohma, H ;

Kita, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6193-6196

[9] A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols [J].

Dohi, Toshifumi ;

Maruyama, Akinobu ;

Takenaga, Naoko ;

Senami, Kento ;

Minamitsuji, Yutaka ;

Fujioka, Hiromichi ;

Caemmerer, Simon B. ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3787-3790

[10] Hypervalent iodine reagents as a new entrance to organocatalysts [J].

Dohi, Toshifumi ;

Kita, Yasuyuki .

CHEMICAL COMMUNICATIONS, 2009, (16) :2073-2085

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