Total Synthesis of (±)-δ-Rubromycin

被引：30

作者：

Wang, Wenjing ^{[1
]}

Xue, Jijun ^{[1
]}

Tian, Tian ^{[1
]}

Zhang, Jie ^{[1
]}

Wei, Liping ^{[1
]}

Shao, Jidong ^{[1
]}

Xie, Zhixiang ^{[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 | 2013年 / 15卷 / 10期

关键词：

ALTERNATIVE SPIROKETALIZATION METHODS; GAMMA-RUBROMYCIN; NAPHTHALENE PORTION; EFFICIENT SYNTHESIS; CONVERGENT ROUTE; HUMAN TELOMERASE; PURPUROMYCIN; HELIQUINOMYCIN; (+/-)-GAMMA-RUBROMYCIN; DERIVATIVES;

D O I：

10.1021/ol400864f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition-metal-catalyzed spiroketalization cyclization has been performed successfully and has led to the first total synthesis of (+/-)-delta-rubromycin with a longest linear sequence of 18 steps from commercially available guaiacol in a 2.7% overall yield.

引用

页码：2402 / 2405

页数：4

共 54 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] Towards the rubromycins: An efficient synthesis of a suitable isocoumarin precursor, its lactam analogue, and palladium-catalyzed couplings [J].

Brasholz, M ;

Luan, XS ;

Reissig, HU .

SYNTHESIS-STUTTGART, 2005, (20) :3571-3580

[5] An expedient and short synthesis of a 6-iodo isocoumarin building block for the rubromycin family and its first palladium-catalyzed couplings [J].

Brasholz, M ;

Reissig, HU .

SYNLETT, 2004, (15) :2736-2738

[6] Rubromycins:: Structurally intriguing, biologically valuable, synthetically challenging antitumour antibiotics [J].

Brasholz, Malte ;

Soergel, Sebastian ;

Azap, Cengiz ;

Reissig, Hans-Ulrich .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (23) :3801-3814

[7] A facile synthesis of fused aromatic spiroacetals based on the 3,4,3′,4′-tetrahydro-2,2′-spirobis(2H-1-benzopyran) skeleton [J].

Brimble, Margaret A. ;

Flowers, Christopher L. ;

Trzoss, Michael ;

Tsang, Kit Y. .

TETRAHEDRON, 2006, 62 (25) :5883-5896

[8] 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-&

[9] RUBROMYCIN, EIN ROTES ANTIBIOTIKUM AUS ACTINOMYCETEN [J].

BROCKMANN, H ;

RENNEBERG, KH .

NATURWISSENSCHAFTEN, 1953, 40 (02) :59-60

[10] RUBROMYCINS .2. [J].

BROCKMANN, H ;

LENK, W ;

SCHWANTJE, G ;

ZEECK, A .

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

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