Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid
Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid
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DOI：
10.1016/j.tetlet.2008.09.144
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发表时间：
2008-12-08
影响因子：
1.8
通讯作者：
Kobayashi, Yuichi
中科院分区：
文献类型：
--
作者：
Ogawa, Narihito;Kobayashi, Yuichi
以(1R，4S)-4-羟基环戊烯-2-烯基乙酸酯(19)为原料，经13步反应制得2-((1R，2S，3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic酸的叔醚(5，相当于表茉莉酸的还原产物)，用氯甲酸异丁酯活化，与异亮氨酸在室温下缩合48h，脱硅氧化成表茉莉酸的异亮氨酸偶合物，三步得率为68%。类似地，合成了表茉莉酸的异亮氨酸异亮氨酸结合物和3种异亮氨酸结合物：表茉莉酸、茉莉酸和对茉莉酸。(C)2008爱思唯尔有限公司。保留所有权利。
The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.