Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates

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	Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates
	Hu TS(胡泰山) ; Yu Q(俞千) ; Wu YL(吴毓林) ; Wu YK(伍贻康)
刊名	J. Org. Chem.
	2001
卷号	66 期号:3 页码:853-861
ISSN号	0022-3263
其他题名	单四氢呋喃环番荔枝内酯的对映体选择性合成
通讯作者	吴毓林
英文摘要	The total synthesis of two mono-THF acetogenins, tonkinecin (1) and annonacin (2), is reported in full detall. Terminal acetylene 3 prepared from D-glucono-δ-lactone and asymmetric dihydroxylation was emplyed as a common intermediate for both targets 1 and 2. Pd(0)-catalyzed coupling reaction of 3 with vinyl iodides 4 and 5, the chiral centers of which were taken from D-xylose and S-(-)-ethyl lactate, afforded enyne 26 and 27, respectively. Selective hydrogenation of 26 or 27 with diimide followed by removal of MOM ethers completed the synthesis of 1 A coupling reaction between the lithium derivative of 3 and epoxide 6 in the presence of boron trifluoride etherate gave 42. Both chiral centers in epoxide 6 were taken from L-ascorbic acid. Subsequent catalytic hydrogenation and MOM protection led to 43b. Introduction of the butenolide moiety by aldol condensation of protected S-lactal followed by cleavage of all MOM ethers completed the synthesis of 2.
学科主题	天然产物有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo005643b
语种	英语
WOS记录号	WOS:000166943800028
公开日期	2013-01-17
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/14002]
专题	上海有机化学研究所_生命有机化学国家重点实验室
推荐引用方式 GB/T 7714	Hu TS,Yu Q,Wu YL,et al. Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates[J]. J. Org. Chem.,2001,66(3):853-861.
APA	胡泰山,俞千,吴毓林,&伍贻康.(2001).Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates.J. Org. Chem.,66(3),853-861.
MLA	胡泰山,et al."Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates".J. Org. Chem. 66.3(2001):853-861.