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

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