Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia.
Org Biomol Chem. 2009 Oct 21;7(20):4296-300. doi: 10.1039/b912233h. Epub 2009 Aug 17.
A five-step synthesis of monoalkyl- and 2,5-dialkyl-1,3-cyclohexanediones (1) is described via a sequence involving sequential Birch reductions and alkylations from the readily accessible and inexpensive starting material, 3,5-dimethoxybenzoic acid. Two approaches were considered in which alkylation at C-2 occurs either prior or subsequent to the proposed reduction. The successful route, in which Birch reduction of a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed for their biological activity via electroantennographic detection.
一种五步法合成单烷基-和 2,5-二烷基-1,3-环己二酮（1）的方法，通过一系列包括连续伯奇还原和烷基化反应，从易得且廉价的起始原料 3,5-二甲氧基苯甲酸开始。考虑了两种方法，其中 C-2 的烷基化反应要么先于，要么后于所提出的还原反应。成功的路线是 3-烷基间苯二酚衍生物（3）的伯奇还原先于烷基化反应，该路线应用于 chiloglottone 1（1dc）的合成中，总收率为 58%。chiloglottone 1 是一类新的天然产物的成员，它代表了 thynnine 黄蜂 Neozeleboria cryptoides 的已知性信息素和澳大利亚性欺骗兰花属 Chiloglottis 的传粉者引诱剂。通过触角电生理检测评估了合成类似物的生物活性。
