Regioselective reactions on a 1,3-disubstituted dihydroxymethyl or dicarboxyl hexahydropentalene skeleton

被引：5

作者：

Tanase, Constantin I. ^{[1
]}

Draghici, Constantin ^{[2
]}

Shova, Sergiu ^{[3
]}

Cojocaru, Ana ^{[1
]}

Maganu, Maria ^{[2
]}

Munteanu, Cristian V. A. ^{[4
]}

Cocu, Florea ^{[1
]}

机构：

[1] Natl Inst Chem Pharmaceut Res & Dev, Bucharest 031299 3, Romania

[2] Organ Chem Ctr CD Nenitescu, Bucharest 060023, Romania

[3] Inst Macromol Chem Petru Poni, Iasi, Romania

[4] Romanian Acad Inst Biochem IBAR, Bucharest 060031, Romania

来源：

TETRAHEDRON | 2015年 / 71卷 / 38期

关键词：

MCPBA lactonization; Haloetherification; Halolactonization; Oxymercuration-demercuration; Hexahydropentalene; X-ray crystallography; CARBOXYLIC-ACIDS; SOLVOMERCURATION-DEMERCURATION; OXYMERCURATION-DEMERCURATION; PROTECTED DERIVATIVES; HOMOALLYLIC ALCOHOLS; OLEFINS; TETRAHYDROFURANS; ADDITIONS; TRIFLATE;

D O I：

10.1016/j.tet.2015.07.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

lodo-, bromo-, chloro-etherification and oxymercuration-demercuration of hexahydropentalene 1,3-dimethanol were regioselectively realized with formation of pentalenofurane compounds in good yields. The corresponding hexahydropentaleno diacid and its monoester react regioselectively with MCPBA to give two gamma-lactones. Haloetherification of the diacid also regioselectively gives halogenolactones in good yield. A new method for synthesis of a bislactone was developed in better yield (79%) than that presented in the literature (58%). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6852 / 6859

页数：8

共 25 条

[1] IODOENOLCYCLIZATION .3. A GENERAL-APPROACH TO TETRASUBSTITUTED FURANS FROM 2-ALKENYL-1,3-DICARBONYL COMPOUNDS [J].

ANTONIOLETTI, R ;

CECCHINI, C ;

CIANI, B ;

MAGNANTI, S .

TETRAHEDRON LETTERS, 1995, 36 (49) :9019-9022

[2] PREDICTIVE MODELS FOR THE OVERALL 5-ENDO-TRIG IODOCYCLISATION OF HOMOALLYLIC ALCOHOLS [J].

BARKS, JM ;

KNIGHT, DW ;

SEAMAN, CJ ;

WEINGARTEN, GG .

TETRAHEDRON LETTERS, 1994, 35 (39) :7259-7262

[3] IODOETHERIFICATION OF HOMOALLYLIC ALCOHOLS - A STEREOSELECTIVE APPROACH TO TETRAHYDROFURANS [J].

BEDFORD, SB ;

BELL, KE ;

FENTON, G ;

HAYES, CJ ;

KNIGHT, DW ;

SHAW, D .

TETRAHEDRON LETTERS, 1992, 33 (43) :6511-6514

[4] IODINE-INDUCED CYCLIZATIONS OF (E)-3-HYDROXY-5-ALKENOATES AND (Z)-3-HYDROXY-5-ALKENOATES - STEREOSELECTIVE APPROACHES TO TRISUBSTITUTED TETRAHYDROFURANS [J].

BENNETT, F ;

BEDFORD, SB ;

BELL, KE ;

FENTON, G ;

KNIGHT, DW ;

SHAW, D .

TETRAHEDRON LETTERS, 1992, 33 (43) :6507-6510

[5] SOLVOMERCURATION-DEMERCURATION .6. ADDITIONS TO BICYCLIC OLEFINS .10. STEREOCHEMISTRY OF OXYMERCURATION-DEMERCURATION OF CIS-BICYCLO[3.3.0]OCT-2-ENE, ENDO-TRIMETHYLENE-NORBORN-8-ENE AND RELATED OLEFINS [J].

BROWN, HC ;

HAMMAR, WJ .

TETRAHEDRON, 1978, 34 (23) :3405-3411

[6] SOLVOMERCURATION-DEMERCURATION .1. OXYMERCURATION-DEMERCURATION OF REPRESENTATIVE OLEFINS IN AN AQUEOUS SYSTEM - A CONVENIENT MILD PROCEDURE FOR MARKOVNIKOV HYDRATION OF CARBON-CARBON DOUBLE BOND [J].

BROWN, HC ;

GEOGHEGA.PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1844-&

[7] AN IMPROVED SYNTHESIS OF DESLONGCHAMPS DIKETONE BY DIRECT REGIOSELECTIVE FUNCTIONALIZATION OF ENDO-DICYCLOPENTADIENE [J].

CARCELLER, E ;

GARCIA, ML ;

MOYANO, A ;

SERRATOSA, F .

SYNTHETIC COMMUNICATIONS, 1985, 15 (11) :951-958

[8] Efficient Medium Ring Size Bromolactonization Using a Sulfur-Based Zwitterionic Organocatalyst [J].

Cheng, Yi An ;

Chen, Tao ;

Tan, Chong Kiat ;

Heng, Jun Jie ;

Yeung, Ying-Yeung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (40) :16492-16495

[9] Lewis base catalysis of bromo- and iodolactonization, and cycloetherification [J].

Denmark, Scott E. ;

Burk, Matthew T. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) :20655-20660

[10] Efficient Intramolecular Hydroalkoxylation/Cyclization of Unactivated Alkenols Mediated by Lanthanide Triflate Ionic Liquids [J].

Dzudza, Alma ;

Marks, Tobin J. .

ORGANIC LETTERS, 2009, 11 (07) :1523-1526

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