Synthesis of Dibromophakellin, Dibromophakellstatin, and Dibromoagelaspongin via Oxidative Cyclization of Dihydrooroidin Derivatives

被引：23

作者：

Feldman, Ken S. ^{[1
]}

Fodor, Matthew D. ^{[1
]}

Skoumbourdis, Amanda P. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

SYNTHESIS-STUTTGART | 2009年 / 18期

基金：

美国国家科学基金会;

关键词：

oxidative cyclization; Pummerer; marine alkaloid; PUMMERER REACTION CHEMISTRY; PYRROLE-IMIDAZOLE ALKALOIDS; POLYVALENT IODINE; OROIDIN; FUNCTIONALIZATION; SUBSTITUTION; INVOLVEMENT; PALAUAMINE; INHIBITOR; SPONGES;

D O I：

10.1055/s-0029-1216939x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Putative biosynthesis proposal for oroidin-derived marine alkaloids serves as a template for developing a biomimetic strategy for the syntheses of tetracyclic members of the phakellin family of sponge metabolites. Pummerer chemistry triggers the oxidative cyclization of the dihydrooroidin derivative, and dibromophakellin, dibromophakellstatin, and dibromoagelaspongin all can be accessed efficiently via this strategy.

引用

页码：3162 / 3173

页数：12

共 61 条

[1]

Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237

[2] 2(1H)-QUINOLINONES WITH CARDIAC STIMULANT ACTIVITY .3. SYNTHESIS AND BIOLOGICAL PROPERTIES OF 6-IMIDAZOL-1-YL DERIVATIVES [J].

BELL, AS ;

CAMPBELL, SF ;

MORRIS, DS ;

ROBERTS, DA ;

STEFANIAK, MH .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1552-1558

[3] REGIOSPECIFIC SYNTHESIS OF THE AMINOIMIDAZOQUINOXALINE (IQX) MUTAGENS FROM COOKED FOODS [J].

BIERER, DE ;

OCONNELL, JF ;

PARQUETTE, JR ;

THOMPSON, CM ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1390-1405

[4] Revised structure of palau'amine [J].

Buchanan, Malcolm S. ;

Carroll, Anthony R. ;

Quinn, Ronald J. .

TETRAHEDRON LETTERS, 2007, 48 (26) :4573-4574

[5] 2,5-DILITHIATION OF N-PROTECTED IMIDAZOLES - SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES OF 1-METHOXYMETHYL-IMIDAZOLE, 1-TRIPHENYLMETHYL-IMIDAZOLE, AND 1-(N,N-DIMETHYLSULPHONAMIDO)-IMIDAZOLE [J].

CHADWICK, DJ ;

NGOCHINDO, RI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :481-486

[6] Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead [J].

Chauvière, G ;

Bouteille, B ;

Enanga, B ;

de Albuquerque, C ;

Croft, SL ;

Dumas, M ;

Périé, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (03) :427-440

[7] Hypervalent iodine-mediated vicinal syn diazidation:: Application to the total synthesis of (±)-dibromophakellstatin [J].

Chung, R ;

Yu, ES ;

Incarvito, CD ;

Austin, DJ .

ORGANIC LETTERS, 2004, 6 (22) :3881-3884

[8] New methods of imidazole functionalization - From imidazole to marine alkaloids [J].

Du, Hongwang ;

He, Yong ;

Sivappa, Rasapalli ;

Lovely, Carl J. .

SYNLETT, 2006, (07) :965-992

[9]

FAULKNER DJ, 1974, SEA, V5, P679

[10] THE STRUCTURE OF DIBROMOAGELASPONGIN - A NOVEL BROMINE-CONTAINING GUANIDINE DERIVATIVE FROM THE MARINE SPONGE AGELAS-SP [J].

FEDOREYEV, SA ;

ILYIN, SG ;

UTKINA, NK ;

MAXIMOV, OB ;

RESHETNYAK, MV ;

ANTIPIN, MY ;

STRUCHKOV, YT .

TETRAHEDRON, 1989, 45 (11) :3487-3492

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