使用二氧六环哌啶（一种有前景的手性砌块）简洁且高度立体控制地合成1-脱氧半乳糖野尻霉素及其类似物。

Concise and highly stereocontrolled synthesis of 1-deoxygalactonojirimycin and its congeners using dioxanylpiperidene, a promising chiral building block.

作者信息

Takahata Hiroki, Banba Yasunori, Ouchi Hidekazu, Nemoto Hideo

机构信息

Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.

出版信息

Org Lett. 2003 Jul 10;5(14):2527-9. doi: 10.1021/ol034886y.

DOI:10.1021/ol034886y

PMID:12841772

Abstract

[reaction: see text] A concise and stereoselective synthesis of the chiral building block, dioxanylpiperidene 4 as a precursor for deoxyazasugars, starting from the Garner aldehyde 5 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring is described. The asymmetric synthesis of 1-deoxygalactonojirimycin and its congeners 1-3 was carried out via the use of 4 in a highly stereocontrolled mode.

摘要

[反应：见正文] 描述了一种从加纳醛5开始，使用催化闭环复分解反应（RCM）构建哌啶环，简洁且立体选择性地合成手性砌块二氧杂环戊基哌啶4作为脱氧氮杂糖前体的方法。通过以高度立体控制的方式使用4进行了1-脱氧半乳糖野尻霉素及其同系物1-3的不对称合成。