Use of cycloaddition reactions and photochemical transformations in the preparation of norcarane derivatives

被引：10
|
作者：
Tabarez, Carlos [1 ]
Lopez Radcenco, Andres [2 ]
Moyna, Guillermo [2 ]
机构：
[1] Univ Republica, Fac Quim, Dept Quim Organ, Ave Gen Flores 2124, Montevideo 11800, Uruguay
[2] Univ Republ, CENUR Litoral Norte, Dept Quim Litoral, Ruta 3 Km 363, Paysandu 60000, Uruguay
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 13期
关键词：
beta; gamma-Unsaturated ketone chromophores; Diels-Alder cycloadditions; Norcarane derivatives; Photochemical transformations; MARASMANE SESQUITERPENES; MALEIC ANHYDRIDE; RUSSULA-FOETENS; TROPOLONE; ADDUCTS;
D O I：
10.1016/j.tetlet.2016.02.087
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We detail a strategy for the preparation of bicyclo[4.1.0]heptanes, or norcaranes, based on Diels-Alder reactions and photochemical transformations. As the latter step of the process proceeds with unique regio and stereochemistries, the regio and stereochemical outcome of the overall sequence is dictated by the structures of the diene and dienophile and the conditions used in the initial cycloaddition reaction. This allows for the preparation of norcaranes with different substitution patterns and defined relative stereochemistries, and could be exploited in the design of complex structures bearing this bicyclic moiety. (C) 2016 Elsevier Ltd. All rights reserved.
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页码：1515 / 1517
页数：3
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