Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System

doi:10.1002/asia.201200363

CORC > 化学研究所 > 中国科学院化学研究所

	Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System
	Sun, Tian-Wen 1,2,3; Ren, Wei-Wu 1,2,3; Xiao, Qing 1,2,3; Tang, Ye-Feng 4,5; Zhang, Yan-Dong 6; Li, Yong 1,2,3; Meng, Fan-Ke 1,2,3; Liu, Yi-Fan 1,2,3; Zhao, Ming-Zhe 1,2,3; Xu, Ling-Min 1,2,3
刊名	CHEMISTRY-AN ASIAN JOURNAL
	2012-10-01
卷号	7 期号:10 页码:2321-2333
关键词	Fused-ring Systems Natural Products Schindilactone a Synthetic Methods Total Synthesis
ISSN号	1861-4728
DOI	10.1002/asia.201200363
英文摘要	First-generation synthetic strategies for the diastereoselective total synthesis of schindilactone A (1) are presented and methods for the synthesis of the ABC, FGH, and CDEF moieties are explored. We have established a method for the synthesis of the ABC moiety, which included both a DielsAlder reaction and a ring-closing metathesis as the key steps. We have also developed a method for the synthesis of the FGH moiety, which involved the use of a PausonKhand reaction and a carbonylative annulation reaction as the key steps. Furthermore, we have achieved the construction of the central 78 bicyclic ring system by using a [3,3]-rearrangement as the key step. However, unfortunately, when this rearrangement reaction was applied to the construction of the more advanced CDEF moiety, the anticipated annulation reaction did not occur and the development of an alternative synthetic strategy would be required for the construction of this central core.
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000308877400022
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/49521]
专题	中国科学院化学研究所
通讯作者	Chen, Jia-Hua
作者单位	1.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, BNLMS, Beijing 100871, Peoples R China 2.Peking Univ, Coll Chem, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China 3.Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China 4.Tsinghua Univ, Sch Life Sci, Comprehens AIDS Res Ctr, Beijing 100084, Peoples R China 5.Tsinghua Univ, Sch Med, Beijing 100084, Peoples R China 6.Xiamen Univ, Dept Chem, Xiamen 361005, Peoples R China
推荐引用方式 GB/T 7714	Sun, Tian-Wen,Ren, Wei-Wu,Xiao, Qing,et al. Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System[J]. CHEMISTRY-AN ASIAN JOURNAL,2012,7(10):2321-2333.
APA	Sun, Tian-Wen.,Ren, Wei-Wu.,Xiao, Qing.,Tang, Ye-Feng.,Zhang, Yan-Dong.,...&Yang, Zhen.(2012).Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System.CHEMISTRY-AN ASIAN JOURNAL,7(10),2321-2333.
MLA	Sun, Tian-Wen,et al."Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 1: Construction of the ABC and FGH Ring Systems and Initial Attempts to Construct the CDEF Ring System".CHEMISTRY-AN ASIAN JOURNAL 7.10(2012):2321-2333.