典型文献
Highly Stereocontrolled Total Syntheses of Cedrane Sesquiterpenes via Cascade [5+2] Cycloaddition/Etherification
文献摘要：
Cedrane sesquiterpenes possess common tricyclo[5.3.1.01,5]undecane core structure.The varied oxa-five-membered ring decorating their core structure to form 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework,containing six consecutive chiral centers (including two all-carbon quaternary centers and one oxygenated quaternary carbon center),has proven to be a synthetic challenge and a bio-synthetic mystery to date.Herein,we reported a distinct and biomimetic strategy to these sesquiterpenes resulting in the concise asymmetric total syntheses of three cedrane sesquiterpenes from simple commercially available building blocks.Key feature is ex-ploitation of a cascade oxidative dearomatization-induced[5+2]cycloaddition/etherification to highly stereocontrolled construct 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework with five contiguous chiral centers in one step.In addition,a metal-free i2-catalyzed and DMSO-mediated oxidative dehydroaromatization was applied to prepare curcuphenol and its derivatives from the highly functionalized cyclohexenones with minimal manipulations.
文献关键词：
中图分类号：
作者姓名：
Yuhan Zhang;Zhiyong Chi;Xiangxin Li;Zhixiang Xie
作者机构：
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering,Lanzhou University,222 Tianshui South Road,Lanzhou,Gansu 730000,China
文献出处：
引用格式：
[1]Yuhan Zhang;Zhiyong Chi;Xiangxin Li;Zhixiang Xie-.Highly Stereocontrolled Total Syntheses of Cedrane Sesquiterpenes via Cascade [5+2] Cycloaddition/Etherification)[J].中国化学（英文版）,2022(02):183-189
A类：
Stereocontrolled,Syntheses,Cedrane,Sesquiterpenes,Cycloaddition,Etherification,tricyclo,undecane,tetracyclo,tridecane,cedrane,ploitation,etherification,stereocontrolled,dehydroaromatization,curcuphenol,cyclohexenones
B类：
Highly,Total,via,Cascade,5+2,sesquiterpenes,possess,common,core,structure,varied,oxa,five,membered,ring,decorating,their,form,framework,containing,six,consecutive,chiral,centers,including,two,carbon,quaternary,oxygenated,has,proven,synthetic,challenge,mystery,date,Herein,we,reported,distinct,biomimetic,strategy,resulting,concise,asymmetric,total,syntheses,three,from,simple,commercially,available,building,blocks,Key,feature,cascade,oxidative,dearomatization,induced,cycloaddition,highly,construct,contiguous,step,In,metal,free,i2,catalyzed,DMSO,mediated,was,applied,prepare,its,derivatives,functionalized,minimal,manipulations
AB值：
0.514511
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