Total synthesis of (±)-γ-Rubromycin on the basis of two aromatic pummerer-type reactions

被引：67

作者：

Akai, Shuji

Kakiguchi, Keisuke

Nakamura, Yuka

Kuriwaki, Ikumi

Dohi, Toshifumi

Harada, Shusaku

Kubo, Ozora

Morita, Nobuyoshi

Kita, Yasuyuki

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 39期

关键词：

natural products; Pummerer reaction; rearrangement; spiroketals; total synthesis;

D O I：

10.1002/anie.200702382

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Double or nothing: In a convergent synthesis of the title compound, a potent inhibitor of human telomerase, two different aromatic Pummerer-type reactions were employed to construct the pivotal bisbenzannelated spiroketal skeleton from the two fragments shown in the scheme. This methodology offers convenient access to a wide range of substituted bisbenzannelated spiroketals from naphthol derivatives. MOM = methoxymethyl. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：7458 / 7461

页数：4

相关论文

共 47 条

[1] Regioselective, nucleophilic carbon-carbon bond formation at the C4-position of indoles initiated by the aromatic Pummerer-type reaction [J].

Akai, S ;

Kawashita, N ;

Wada, Y ;

Satoh, H ;

Alinejad, AH ;

Kakiguchi, K ;

Kuriwaki, I ;

Kita, Y .

TETRAHEDRON LETTERS, 2006, 47 (12) :1881-1884

[2] Highly regioselective nucleophilic carbon-carbon bond formation on furans and thiophenes initiated by Pumerer-type reaction [J].

Akai, S ;

Kawashita, N ;

Satoh, H ;

Wada, Y ;

Kakiguchi, K ;

Kuriwaki, I ;

Kita, Y .

ORGANIC LETTERS, 2004, 6 (21) :3793-3796

[3]

Akai S, 2002, HETEROCYCLES, V58, P75

[4] AN EFFICIENT SYNTHESIS OF P-QUINONES UTILIZING A NOVEL PUMMERER-TYPE REARRANGEMENT OF P-SULFINYLPHENOLS [J].

AKAI, S ;

TAKEDA, Y ;

LIO, K ;

YOSHIDA, Y ;

KITA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) :1013-1014

[5] Novel ipso-substitution of p-sulfinylphenols through the Pummerer-type reaction: A selective and efficient synthesis of p-quinones and protected p-dihydroquinones [J].

Akai, S ;

Takeda, Y ;

Iio, K ;

Takahashi, K ;

Fukuda, N ;

Kita, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5526-5536

[6] Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings:: A convergent synthesis of diverse benzofuran neolignans [J].

Akai, S ;

Morita, N ;

Iio, K ;

Nakamura, Y ;

Kita, Y .

ORGANIC LETTERS, 2000, 2 (15) :2279-2282

[7] Recent advances in Pummerer reactions [J].

Akai, Shuji ;

Kita, Yasuyuki .

SULFUR-MEDIATED REARRANGEMENTS I, 2007, 274 :35-76

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

BARDONE, MR ;

MARTINELLI, E ;

ZERILLI, LF ;

CORONELLI, C .

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

[9] 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

[10]

BRASHOLZ M, 2005, SYSNTHESIS, P2571

← 1 2 3 4 5 →