迭代苯炔-呋喃环加成反应：对映体-Sch 47554和对映体-Sch 47555全合成的研究

Iterative benzyne-furan cycloaddition reactions: studies toward the total synthesis of ent-Sch 47554 and ent-Sch 47555.

作者信息

Morton Gillian E, Barrett Anthony G M

机构信息

Department of Chemistry, Imperial College London, South Kensington, England.

出版信息

Org Lett. 2006 Jun 22;8(13):2859-61. doi: 10.1021/ol061007+.

DOI:10.1021/ol061007+

PMID:16774275

Abstract

[reaction: see text] 7-Fluoro-5,8-dimethoxy-1-naphthol, prepared from the lithiation and benzyne formation from 1,4-difluoro-2,5-dimethoxybenzene and Diels-Alder cycloaddition with furan, was sequentially C-glycosidated under Suzuki conditions and O-glycosidated using di-O-acetyl-L-rhamnal to provide the corresponding beta-naphthyl C,O-disaccharide. Further lithiation, benzyne formation, and cycloaddition with furan gave an oxa-bridged 1,4-dihydroanthracenyl C,O-disaccharide, a model compound relevant to the total synthesis of Sch 47555.

摘要

[反应：见正文] 7-氟-5,8-二甲氧基-1-萘酚由1,4-二氟-2,5-二甲氧基苯经锂化和苯炔生成，并与呋喃进行狄尔斯-阿尔德环加成反应制得，在铃木条件下依次进行C-糖基化，然后用二-O-乙酰基-L-鼠李糖进行O-糖基化，得到相应的β-萘基C,O-二糖。进一步锂化、苯炔生成以及与呋喃的环加成反应得到了一个氧桥连的1,4-二氢蒽基C,O-二糖，这是一个与Sch 47555全合成相关的模型化合物。