Literature DB >> 23265326

Direct imine acylation: synthesis of the proposed structures of 'upenamide.

William P Unsworth1, Katherine A Gallagher, Mickaël Jean, Jan Peter Schmidt, Louis J Diorazio, Richard J K Taylor.   

Abstract

The synthesis of the two proposed structures of macrocyclic marine natural product 'upenamide is reported. The key step utilizes direct imine acylation (DIA) with a protected β-hydroxy acid to construct the key tricyclic ABC ring system. The macrocyclization was completed in the final step using a Stille cross-coupling reaction.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 23265326     DOI: 10.1021/ol3030764

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  A concise Diels-Alder strategy leading to congeners of the ABC ring system of the marine alkaloid 'upenamide.

Authors:  Marta E Wenzler; Bruce J Melancon; Gary A Sulikowski
Journal:  Tetrahedron Lett       Date:  2016-06-07       Impact factor: 2.415

2.  From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis.

Authors:  Sarah J Chambers; Graeme Coulthard; William P Unsworth; Peter O'Brien; Richard J K Taylor
Journal:  Chemistry       Date:  2016-03-23       Impact factor: 5.236

3.  Silver Catalyzed Decarbonylative [3 + 2] Cycloaddition of Cyclobutenediones and Formamides.

Authors:  Pengcheng Wang; Ruirui Yu; Sajjad Ali; Zhengshen Wang; Zhigang Liu; Jinming Gao; Huaiji Zheng
Journal:  Molecules       Date:  2021-05-17       Impact factor: 4.411

Review 4.  Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors:  Xufen Yu; Dianqing Sun
Journal:  Molecules       Date:  2013-05-24       Impact factor: 4.411

5.  Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.

Authors:  Thomas C Stephens; Aggie Lawer; Thomas French; William P Unsworth
Journal:  Chemistry       Date:  2018-08-19       Impact factor: 5.236

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.