Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine

Hwayoung Yun; Jongmin Kim; Jaehoon Sim; Sujin Lee; Young Taek Han; Dong Jo Chang; Dae Duk Kim; Young Ger Suh

doi:10.1021/jo300309z

Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine

Hwayoung Yun, Jongmin Kim, Jaehoon Sim, Sujin Lee, Young Taek Han, Dong Jo Chang, Dae Duk Kim, Young Ger Suh

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.

Original language	English
Pages (from-to)	5389-5393
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	77
Issue number	12
DOIs	https://doi.org/10.1021/jo300309z
Publication status	Published - 15 Jun 2012

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title = "Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine",

abstract = "Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.",

author = "Hwayoung Yun and Jongmin Kim and Jaehoon Sim and Sujin Lee and Han, {Young Taek} and Chang, {Dong Jo} and Kim, {Dae Duk} and Suh, {Young Ger}",

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T1 - Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine

AU - Yun, Hwayoung

AU - Kim, Jongmin

AU - Sim, Jaehoon

AU - Lee, Sujin

AU - Han, Young Taek

AU - Chang, Dong Jo

AU - Kim, Dae Duk

AU - Suh, Young Ger

PY - 2012/6/15

Y1 - 2012/6/15

N2 - Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.

AB - Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.

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Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine

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