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1-（-1-芳基丙烯酰基-3-基）-3,4,6-三-O-苄基-D-葡萄糖烯的合成、结构表征及其转化为五取代（2,3,4）-色满：钯催化的交叉脱氢偶联反应

Synthesis and Structural Characterization of 1-(-1-Arylpropenon-3-yl)-3,4,6-tri--benzyl-d-glucals and Their Transformation into Pentasubstituted (2,3,4)-Chromanes Pd-Catalyzed Cross Dehydrogenative Coupling Reaction.

作者信息

Shankar Bhawani, Khatri Vinod, Kumar Banty, Maikhuri Vipin K, Kumar Amit, Tomar Rashmi, Prasad Ashok K

机构信息

Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India.

Department of Chemistry, Deshbandhu College, University of Delhi, Delhi 110019, India.

出版信息

ACS Omega. 2021 Apr 22;6(17):11248-11259. doi: 10.1021/acsomega.1c00103. eCollection 2021 May 4.

DOI:10.1021/acsomega.1c00103
PMID:34056280
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8153922/
Abstract

We have developed an efficient methodology for the synthesis of (2,3,4)-2-hydroxymethyl-3,4-dihydroxy-6-aryl-7-aroylchromanes in which the chirality at the -2, -3, and -4 positions is being drawn from -glucopyranosyl aldehyde, which in turn can be efficiently synthesized from d-glucose. Thus, the synthesis starts with the transformation of sugar aldehyde into 1-(-1-arylpropenon-3-yl)-3,4,6-tri--benzyl-d-glucals using Claisen-Schmidt type condensation reaction with different acetophenones and then to 1,2-disubstituted glucals Pd(II)-catalyzed cross dehydrogenative coupling reaction, which in turn has been efficiently converted into (2,3,4)-chromanes 6π-electrocyclization and dehydrogenative aromatization.

摘要

我们已经开发出一种高效的方法来合成(2,3,4)-2-羟甲基-3,4-二羟基-6-芳基-7-芳酰基色满，其中-2、-3和-4位的手性来自于葡萄糖醛，而葡萄糖醛又可以由d-葡萄糖高效合成。因此，合成过程始于通过与不同苯乙酮的克莱森-施密特型缩合反应将糖醛转化为1-(-1-芳基丙烯酮-3-基)-3,4,6-三--苄基-d-葡萄糖烯丙醛，然后通过钯(II)催化的交叉脱氢偶联反应转化为1,2-二取代的葡萄糖烯丙醛，进而通过6π-电环化和脱氢芳构化高效转化为(2,3,4)-色满。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/816e5a872800/ao1c00103_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/0e8e00400d2d/ao1c00103_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/00f26df7a4b9/ao1c00103_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/1aab343488b4/ao1c00103_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/66a2c224ce97/ao1c00103_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/a69e3f14c832/ao1c00103_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/b2ed6b523299/ao1c00103_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/816e5a872800/ao1c00103_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/0e8e00400d2d/ao1c00103_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/00f26df7a4b9/ao1c00103_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/1aab343488b4/ao1c00103_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/66a2c224ce97/ao1c00103_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/a69e3f14c832/ao1c00103_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/b2ed6b523299/ao1c00103_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0e7/8153922/816e5a872800/ao1c00103_0003.jpg

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