Cascade Polyketide and Polyene Cyclizations: Biomimetic Total Synthesis of Hongoquercin B

被引：29

作者：

Barrett, Tim N. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 49期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; ABSOLUTE-CONFIGURATION; FUNGAL METABOLITE; NATURAL-PRODUCTS; METHYL-ETHER; SICCANIN; AROMATIZATION; (-)-SICCANIN; INHIBITOR; QUINONES;

D O I：

10.1021/ja511534x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of hongoquercin B was carried out in 9 steps from trans,trans-farnesyl acetate using a palladium catalyzed decarboxylative pi-farnesyl rearrangement of a diketo-dioxinone ester, aromatization and cationic diene-epoxide cyclization as key steps. This cascade tetracyclization simplifies the synthesis of terpenoid resorcylate natural products.

引用

页码：17013 / 17015

页数：3

共 31 条

[1] Mechanistic studies of highly regioselective decarboxylative-prenyl migration reactions of prenyloxycarbonyl-diketo-dioxinones [J].

Anderson, Katie ;

Laclef, Sylvain ;

Barrett, Anthony G. M. .

TETRAHEDRON, 2014, 70 (35) :5569-5579

[2] Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds [J].

Barrero, AF ;

Alvarez-Manzaneda, EJ ;

Herrador, MM ;

Chahboun, R ;

Galera, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2325-2328

[3] Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation-Aromatization Sequences [J].

Cordes, Jens ;

Calo, Frederick ;

Anderson, Katie ;

Pfaffeneder, Toni ;

Laclef, Sylvain ;

White, Andrew J. P. ;

Barrett, Anthony G. M. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :652-657

[4] A MECHANISTICALLY DESIGNED BIS-CINCHONA ALKALOID LIGAND ALLOWS POSITION-SELECTIVE AND ENANTIOSELECTIVE DIHYDROXYLATION OF FARNESOL AND OTHER OLIGOPRENYL DERIVATIVES AT THE TERMINAL ISOPROPYLIDENE UNIT [J].

COREY, EJ ;

NOE, MC ;

LIN, SZ .

TETRAHEDRON LETTERS, 1995, 36 (48) :8741-8744

[5] Enantioselective Total Synthesis of the Potent Anti-inflammatory (+)-Myrrhanol A [J].

Domingo, Victoriano ;

Silva, Lucia ;

Dieguez, Horacio R. ;

Arteaga, Jesus F. ;

Quilez del Moral, Jose F. ;

Barrero, Alejandro F. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6151-6156

[6] Inducers of Hypoxic Response: Marine Sesquiterpene Quinones Activate HIF-1 [J].

Du, Lin ;

Zhou, Yu-Dong ;

Nagle, Dale G. .

JOURNAL OF NATURAL PRODUCTS, 2013, 76 (06) :1175-1181

[7] Marine natural products as antituberculosis agents [J].

El Sayed, KA ;

Bartyzel, P ;

Shen, XY ;

Perry, TL ;

Kjawiony, JK ;

Hamann, MT .

TETRAHEDRON, 2000, 56 (07) :949-953

[8] Meroterpenoids produced by fungi [J].

Geris, Regina ;

Simpson, Thomas J. .

NATURAL PRODUCT REPORTS, 2009, 26 (08) :1063-1094

[9] Marine Natural Products as Lead Anti-HIV Agents [J].

Gochfeld, D. J. ;

El Sayed, K. A. ;

Yousaf, M. ;

Hu, J. F. ;

Bartyzel, P. ;

Dunbar, D. C. ;

Wilkins, S. P. ;

Zjawiony, J. K. ;

Schinazi, R. F. ;

Wirtz, S. Schlueter ;

Tharnish, P. M. ;

Hamann, M. T. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2003, 3 (05) :401-424

[10] Cytotoxic Terpene Quinones from Marine Sponges [J].

Gordaliza, Marina .

MARINE DRUGS, 2010, 8 (12) :2849-2870

← 1 2 3 4 →