Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1

被引：75

作者：

Clift, Michael D. ^{[1
]}

Thomson, Regan J. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 40期

关键词：

CARBON BOND FORMATION; TRIMETHYLSILYL ENOL ETHERS; FRIEDEL-CRAFTS ALKYLATION; MUKAIYAMA ALDOL REACTION; DILITHIOMETHANE EQUIVALENT; BACTERIAL PRODIGININES; 1,4-DIKETONES; ENONES; ROSEOPHILIN; ANTICANCER;

D O I：

10.1021/ja906122g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A merged conjugate addition/oxidative coupling sequence that represents an efficient strategy for preparing structurally diverse pyrroles has been developed. Success of the method hinged upon the controlled oxidative coupling of unsymmetrical silyl bis-enol ether intermediates, formed by the 1,4-addition of a Grignard reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.

引用

页码：14579 / 14583

页数：5

共 43 条

[21] A prodigiosin from the roseophilin producer Streptomyces griseoviridis [J].

Kawasaki, Takashi ;

Sakurai, Fumi ;

Hayakawa, Yoichi .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (07) :1265-1267

[22]

KOBAYASHI Y, 1977, TETRAHEDRON LETT, P3741

[23] Potent in vitro anticancer activity of metacycloprodigiosin and undecylprodigiosin from a sponge-derived actinomycete Saccharopolyspora sp nov. [J].

Liu, R ;

Cui, CB ;

Duan, L ;

Gu, QQ ;

Zhu, WM .

ARCHIVES OF PHARMACAL RESEARCH, 2005, 28 (12) :1341-1344

[24] Copper-catalyzed enantioselective conjugate addition of Grignard reagents to acyclic enones [J].

López, F ;

Harutyunyan, SR ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) :12784-12785

[25] GENERATION OF CATION RADICALS FROM ENAMINES AND THEIR REACTIONS WITH OLEFINS [J].

NARASAKA, K ;

OKAUCHI, T ;

TANAKA, K ;

MURAKAMI, M .

CHEMISTRY LETTERS, 1992, (10) :2099-2102

[26] Regio- and enantioselective carbolithiation of non-activated C=C bonds [J].

Norsikian, S ;

Baudry, M ;

Normant, JF .

TETRAHEDRON LETTERS, 2000, 41 (34) :6575-6578

[27] Highly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with α-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis [J].

Palomo, C ;

Oiarbide, M ;

Kardak, BG ;

García, JM ;

Linden, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4154-4155

[28] New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation [J].

Paras, NA ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4370-4371

[29] USE OF A DILITHIOMETHANE EQUIVALENT IN A NOVEL ONE-FLASK [2 + 1 + 2] CYCLOPENTANNULATION REACTION - A HIGHLY EFFICIENT TOTAL SYNTHESIS OF (+/-)-HIRSUTENE [J].

RAMIG, K ;

KUZEMKO, MA ;

MCNAMARA, K ;

COHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1968-1969

[30] A concise synthesis of butylcycloheptylprodigiosin [J].

Reeves, Jonathan T. .

ORGANIC LETTERS, 2007, 9 (10) :1879-1881

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