活性天然产物莪术烯的全合成  

Total synthesis of bioactive natural product Curzerene

作　　者：郭晶晶[1,2] 袁长春 傅凯 荀苗苗 马文兵[1] 王志强[1] 李志春[1] GUO Jing-Jing;YUAN Chang-Chun;FU Kai;XUN Miao-Miao;MA Wen-Bing;WANG Zhi-Qiang;LI Zhi-Chun(School of Chemistry and Chemical Engineering,North University of China,Taiyuan 030051,China;Dezhou Industrial Technology Research Institute,North University of China,Dezhou 253034,China)

机构地区：[1]中北大学化学与化工学院,太原030051 [2]中北大学德州产业技术研究院,德州253034

出　　处：《四川大学学报（自然科学版）》2023年第3期129-134,共6页Journal of Sichuan University(Natural Science Edition)

基　　金：山西省基础研究计划(20210302123016)。

摘　　要：莪术烯(Curzerene)是从姜黄属植物的根茎中分离提取的萜烯呋喃类天然产物,具有抗炎、抗癌、抗利什曼病等多种生物活性.本文以商业化试剂(+)-马鞭草烯酮(6)为手性原料,首先通过已知的3步反应得到关键酮化合物(4);4再与1,1-二甲氧基丙酮发生由TiCl4-Et_3N介导的用于构建丁烯酸内酯的串联环化反应,分别以56%和20%的收率得到天然产物isogermafurenolid(2)及其异构体8-epi-isogermafurenolid(2');最后,2与2'经DIBAL-H还原、酸促进脱水呋喃化一锅反应,以82%的收率合成了目标天然产物莪术烯.该合成路线共5步,总收率34%.Curzerene is a natural product of terpene furans isolated from the curcuma rhizomes,which has various biological activities such as anti-inflammation,anti-cancer and anti-leishmaniasis.In this paper,commercially available(+)-verbenone(6)was utilized as chiral starting material to synthesize Curzerene in 5 steps with 34%total yield.A key ketone compound 4 was first obtained through a known three-step reaction.Then ketone 4 and 1,1-dimethoxyacetone underwent TiCl4-Et3N-mediated cyclization reaction to afford natural products isogermafurenolid(2)and its isomer 8-epi-isogermafurenolid(2′)in 56%and 20%yield,respectively.Finally,the target Curzerene was synthesized from 2 and 2′with 82%yield by a one-pot reaction of DIBAL-H reduction and subsequent acid promoted dehydration.

关 键 词：温莪术 榄香烯型倍半萜 莪术烯 全合成 

分 类 号：O629.9[理学—有机化学]