Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3:   The Final Phase and Completion

doi:10.1002/asia.201200365

CORC > 北京大学 > 化学与分子工程学院

	Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion
	Ren, Wei-Wu ; Chen, Zhi-Xing ; Xiao, Qing ; Li, Yong ; Sun, Tian-Wen ; Zhang, Zi-Yang ; Ye, Qin-Da ; Meng, Fan-Ke ; You, Lin ; Zhao, Ming-Zhe ; Xu, Ling-Min ; Tang, Ye-Feng ; Chen, Jia-Hua ; Yang, Zhen
刊名	chemistry an asian journal
	2012
关键词	fused-ring systems natural products schindilactone A synthetic methods total synthesis RING-CLOSING METATHESIS ALKYL 2-ARYLALKANOATES COUPLING REACTIONS REARRANGEMENT COMPLEXES ADDITIONS CARBONYL ROUTE NORTRITERPENOIDS CONSTRUCTION
DOI	10.1002/asia.201200365
英文摘要	The final phase for the total synthesis of (+/-)-schindilactone A (1) is described herein. Two independent synthetic approaches were developed that featured Pdthiourea-catalyzed cascade carbonylative annulation reactions to construct intermediate 3 and a RCM reaction to make intermediate 4. Other important steps that enabled the completion of the synthesis included: 1) A Ag-mediated ring-expansion reaction to form vinyl bromide 17 from dibromocyclopropane 30; 2) a Pd-catalyzed coupling reaction of vinyl bromide 17 with a copper enolate to synthesize ketoester 16; 3) a RCM reaction to generate oxabicyclononenol 10 from diene 11; 4) a cyclopentenone fragment in substrate 8 was constructed through a Cothiourea-catalyzed PausonKhand reaction (PKR); 5) a Dieckmann-type condensation to successfully form the A ring of schindilactone A (1). The chemistry developed for the total synthesis of schindilactone A (1) will shed light on the synthesis of other family members of schindilactone A.; Chemistry, Multidisciplinary; SCI(E); EI; 10; ARTICLE; 10; 2341-2350; 7
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/231238]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Ren, Wei-Wu,Chen, Zhi-Xing,Xiao, Qing,et al. Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion[J]. chemistry an asian journal,2012.
APA	Ren, Wei-Wu.,Chen, Zhi-Xing.,Xiao, Qing.,Li, Yong.,Sun, Tian-Wen.,...&Yang, Zhen.(2012).Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion.chemistry an asian journal.
MLA	Ren, Wei-Wu,et al."Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion".chemistry an asian journal (2012).