Khupse Rahul S, Erhardt Paul W
Center for Drug Design and Development, College of Pharmacy, The University of Toledo, Toledo, Ohio 43606-3390, USA.
J Nat Prod. 2007 Sep;70(9):1507-9. doi: 10.1021/np070158y. Epub 2007 Sep 11.
The total synthesis of xanthohumol (1) was accomplished in 10% overall yield from phloracetophenone after six steps. Insertion of a prenyl group onto the aryl ring was achieved by a para-Claisen rearrangement after using a Mitsunobu reaction to establish the key prenyl ether precursor. A Claisen-Schmidt condensation was deployed to construct the chalcone scaffold followed by removal of MOM protecting groups under acidic conditions that were optimized to prevent concomitant cyclization to the flavone.
从间苯二酚苯乙酮出发，经过六步反应，以10%的总收率完成了黄腐酚（1）的全合成。在使用 Mitsunobu 反应建立关键的异戊烯基醚前体后，通过对氯克莱森重排将异戊烯基引入芳环。采用克莱森 - 施密特缩合反应构建查尔酮骨架，随后在优化的酸性条件下去除甲氧基甲基（MOM）保护基，以防止同时环化生成黄酮。
