Synthesis ( IF 2.2 ) Pub Date : 2017-07-27 , DOI: 10.1055/s-0036-1590799 Fernando Coelho 1 , Erica da Silva 1 , Nathália Yamakawa 1 , Alcindo Dos Santos 2
Abstract
We described herein a total synthesis of 1,4-dideoxy-1,4-imino-l-arabinitol [(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol, LAB-1], a polyhydroxylated pyrrolidine, which has been demonstrated to be a selective and potent α-glycosidase inhibitor. The main features of our approach are its shortness, efficiency, and simplicity. The total synthesis was accomplished in 6 steps with an overall yield of 12%, starting from a chiral optically active Morita–Baylis–Hillman (MBH) adduct prepared (without epimerization), from Garner’s aldehyde. As far as we know, this is the first report describing the total synthesis of this biologically active pyrrolidine by exploring the synthetic versatility of a MBH adduct.
We described herein a total synthesis of 1,4-dideoxy-1,4-imino-l-arabinitol [(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol, LAB-1], a polyhydroxylated pyrrolidine, which has been demonstrated to be a selective and potent α-glycosidase inhibitor. The main features of our approach are its shortness, efficiency, and simplicity. The total synthesis was accomplished in 6 steps with an overall yield of 12%, starting from a chiral optically active Morita–Baylis–Hillman (MBH) adduct prepared (without epimerization), from Garner’s aldehyde. As far as we know, this is the first report describing the total synthesis of this biologically active pyrrolidine by exploring the synthetic versatility of a MBH adduct.
中文翻译:
短和非对映选择性全合成的多羟基吡咯烷LAB-1:一种有效的α-糖苷酶抑制剂。
摘要
我们在本文中描述了1,4-二脱氧-1,4-亚氨基-1-阿拉伯糖醇[(2 S,3 S,4 S)-2-(羟甲基)吡咯烷-3,4-二醇,LAB-1的全合成〕,一种多羟基化的吡咯烷,已被证明是一种选择性和有效的α-糖苷酶抑制剂。我们方法的主要特点是它的简短,高效和简单。从Garner醛制备的手性旋光活性Morita-Baylis-Hillman(MBH)加合物开始(不进行差向异构化),整个过程分6个步骤完成,总产率为12%。据我们所知,这是第一个通过探索MBH加合物的合成多功能性来描述这种具有生物活性的吡咯烷的全合成的报告。
我们在本文中描述了1,4-二脱氧-1,4-亚氨基-1-阿拉伯糖醇[(2 S,3 S,4 S)-2-(羟甲基)吡咯烷-3,4-二醇,LAB-1的全合成〕,一种多羟基化的吡咯烷,已被证明是一种选择性和有效的α-糖苷酶抑制剂。我们方法的主要特点是它的简短,高效和简单。从Garner醛制备的手性旋光活性Morita-Baylis-Hillman(MBH)加合物开始(不进行差向异构化),整个过程分6个步骤完成,总产率为12%。据我们所知,这是第一个通过探索MBH加合物的合成多功能性来描述这种具有生物活性的吡咯烷的全合成的报告。