各位化学同仁:
十月申城,依旧烟水迷离;深秋津门,已近落叶空山。2020年第四期药明康德有机合成路线设计擂台赛近日于上海、武汉、天津、南通及成都天南地北五个赛区吹响号角,并圆满收场。
夜色寒凉,但非独自清欢,药明康德化学技术部依旧秉持朴素的情感,与大家分享最新整理的竞赛试题。霜降已过,昼短夜长,若您此时打算执笔书写,来不及送上秋天的奶茶,唯有轻声提醒:多喝热水……
文末附有往期竞赛试题,供君一览。本期试题解析仍旧以网络直播的形式于近日择时分享,敬请关注!
1. 请写出以下多步转化的产物结构(每题4分,最后两题每空2分,共计20分;相对构型需要标注明确)。Please provide the structures of products after multi-step transformations (20 points, 4 points for each and 2 points for each blank in the last two questions; the relative configuration needs to be clearly labeled).
2. 设计两条路线合成以下化合物。注意:七元环需要合成(20分)。Please propose two reasonable synthetic routes to synthesize below target starting from commercially available reagents. Note: the seven-membered ring needs to be synthesized (20 points).
3. 使用不同的关环策略设计两条路线合成以下化合物(20分)。Please propose two reasonable synthetic routes to synthesize below target starting from commercially available reagents by two different ring closure strategies (20 points).
4. 使用不同的关环策略设计两条路线合成以下化合物。注意:苯环原料最多有三个取代基(20分)。Please propose two reasonable synthetic routes to synthesize below target starting from commercially available reagents by two different ring closure strategies. Note: The benzene ring material can only have three substituents at most (20 points).
Please propose two reasonable synthetic route to synthesize below racemic target starting from commercially available reagents (20 points).
Please propose one reasonable synthetic route to synthesize below chiral target (20 points).