Enantioselective assembly of the benzo[d]xanthene tetracyclic core of anti-influenza active natural products

被引：32

作者：

Ngoc, Duc Tran ^{[1
]}

Albicker, Martin ^{[1
]}

Schneider, Lorenz ^{[1
]}

Cramer, Nicolai ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, HCI H 304, CH-8093 Zurich, Switzerland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 08期

关键词：

A VIRUS SUBSTANCES; AQUEOUS-SOLUTION; CYCLIZATION; STEREOCHEMISTRY; PDCL3(PYRIDINE)(-); ACETYLSTACHYFLIN; OXYPALLADATION; STACHYFLIN; OXIDATION; REAGENTS;

D O I：

10.1039/c002011g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A combination of an enantioselective conjugate addition/trapping sequence and a ruthenium(III)-catalyzed domino cyclization provides a concise access to benzo[d]xanthenes found in several anti-influenza active sesquiterpene natural products.

引用

页码：1781 / 1784

页数：4

共 20 条

[1] Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].

Albicker, Martin R. ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9139-9142

[2] SOME METABOLITES OF THE MARINE SPONGES SMENOSPONGIA-AUREA AND SMENOSPONGIA (=POLYFIBROSPONGIA) ECHINA [J].

DJURA, P ;

STIERLE, DB ;

SULLIVAN, B ;

FAULKNER, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) :1435-1441

[3] OXIDATION OF OLEFINS BY PALLADIUM(II) .14. PRODUCT DISTRIBUTION AND KINETICS OF THE OXIDATION OF ETHENE BY PDCL3(PYRIDINE)(-) IN AQUEOUS-SOLUTION IN THE PRESENCE AND ABSENCE OF CUCL2 - A MODIFIED WACKER CATALYST WITH ALTERED REACTIVITY [J].

FRANCIS, JW ;

HENRY, PM .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 99 (02) :77-86

[4] Palladium(II)-catalyzed exchange and isomerization reactions .16. The kinetics and stereochemistry of the oxidation and isomerization of hexafluoro allylic alcohols in aqueous solution catalyzed by PdCl3(pyridine)(-) [J].

Francis, JW ;

Henry, PM .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 112 (03) :317-326

[5]

Fürstner A, 2002, ANGEW CHEM INT EDIT, V41, P609

[6] Deuterium-labeling studies establishing stereochemistry at the oxypalladation step in Wacker-type oxidative cyclization of an o-allylphenol [J].

Hayashi, T ;

Yamasaki, K ;

Mimura, M ;

Uozumi, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3036-3037

[7] Transition metal-catalyzed cyclization of 2-allylphenol to 2,3-dihydro-2-methylbenzofuran without β-elimination [J].

Hori, K ;

Kitagawa, H ;

Miyoshi, A ;

Ohta, T ;

Furukawa, I .

CHEMISTRY LETTERS, 1998, (11) :1083-1084

[8] Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp RF-7260 I.: Isolation, structure elucidation and biological activities [J].

Minagawa, K ;

Kouzuki, S ;

Yoshimoto, J ;

Kawamura, Y ;

Tani, H ;

Iwata, T ;

Terui, Y ;

Nakai, H ;

Yagi, S ;

Hattori, N ;

Fujiwara, T ;

Kamigauchi, T .

JOURNAL OF ANTIBIOTICS, 2002, 55 (02) :155-164

[9] Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp RF-7260 II.: Synthesis and preliminary structure-activity relationships of stachyflin derivatives [J].

Minagawa, K ;

Kouzuki, S ;

Kamigauchi, T .

JOURNAL OF ANTIBIOTICS, 2002, 55 (02) :165-171

[10] Regioselective oxidative cation-olefin cyclization of poly-enes:: catalyst turnover via hydride abstraction [J].

Mullen, Charles A. ;

Gagne, Michel R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11880-+

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