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
收藏
页码：6852 / 6859
页数：8
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