Synthesis of Diacetal Trioxa-Cage Compounds via a Sequential Cyclization Reaction of Norbornene Derivatives Induced by Electrophiles.

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题名:	Synthesis of Diacetal Trioxa-Cage Compounds via a Sequential Cyclization Reaction of Norbornene Derivatives Induced by Electrophiles.
作者:	(Hsien-Jen Wu*);(Shih-Hwa Tsai);(Jyh-Haur Chern);林煇章
贡献者:	藥學院藥物化學研究所
日期:	1997-09
上传时间:	2009-08-26 16:26:27 (UTC+8)
摘要:	The synthesis of diacetal trioxa-cage compounds via a sequential cyclization reaction of norbornene derivatives induced by electrophiles in a short sequence is reported. Treatment of the norbornene derivatives 2a-d and 10b with I2 in aqueous THF in the presence of KI at 25 C regioselectively gave the iodo-cage compounds 3a-d and 11 in 80-90% yields, respectively, via a iodine-induced sequential cyclization reaction. No detectable amount of other regioisomers or monocyclization products was obtained. The synthesis of trioxa-cages 14a-e was accomplished from 3a-d and 11 in a two-step sequence. Treatment of diacylnorbornenes 15a-f with I2 in aqueous THF at 25 C regioselectively and stereoselectively gave the sequential cyclization products 16a-f, respectively, which were converted in one step to the diacetal trioxa-cages 24a-f in high yields. The structure of these trioxa-cages was proven by X-ray analysis of the crystalline compound 14e. Other electrophiles, such as bromine, m-CPBA, and Hg(OAc)2, were also found to be effective for the sequential cyclization reaction. Oxymercuration of 15a-f and 2a-c with Hg(OAc)2 in aqueous THF followed by reduction with NaBH4 at 25 C gave compounds 28a-f and 30b,d,c in high yields, respectively.?
關聯:	JOURNAL OF ORGANIC CHEMISTRY 62(18 )6367 ~6373
显示于类别:	[藥物化學研究所] 期刊論文

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