(π-Allyl)palladiurn coupling of 2-(tributylstannyl)cyclopent-2-enone for the synthesis of jasmonoid analogs

被引：3
|
作者：
Parpal, Florencia [1 ]
Pandolfi, Enrique [2 ]
Heguaburu, Viviana [1 ]
机构：
[1] Univ Republ, Ctr Univ Reg Litoral Norte, Dept Quim Litoral, Ruta 3 Km 363, Paysandu 60000, Uruguay
[2] Univ Republica, Fac Quim, Dept Quim Organ, Ave Gen Flores 2124, Montevideo 11800, Uruguay
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 20期
关键词：
C-C coupling; Jasmonoids; (pi-Allyl)palladium; Stille reaction; syn-anti isomerization; METHYL JASMONATE; ACID; DERIVATIVES; STRESS; PLANTS;
D O I：
10.1016/j.tetlet.2017.04.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The coupling of 2-(tributylstannyl)cyclopent-2-enone with several (pi-allyl)palladium complexes derived from allylic electrophiles was investigated as the key step in the synthesis of jasmonoids. These compounds have an important role in plant development, triggering direct and indirect responses when harmed to induce pest resistance. Palladium-catalyzed coupling conditions to obtain a jasmonoid library are described. The retention of geometry of the olefin in the allyl group is not always observed due to synanti isomerization of the (pi-allyl)palladium complex. The methodology was employed for the synthesis of a simplified jasmonic acid analog. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1965 / 1968
页数：4
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