Literature DB >> 20860394

A five-step synthesis of (S)-macrostomine from (S)-nicotine.

Monica F Enamorado1, Pauline W Ondachi, Daniel L Comins.   

Abstract

A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels-Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20860394     DOI： 10.1021/ol101887b

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


  7 in total

1.  An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Authors:  Adam E Goetz; Sarah M Bronner; Jordan D Cisneros; Joshua M Melamed; Robert S Paton; K N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-03       Impact factor: 15.336

2.  Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Authors:  Travis C McMahon; Jose M Medina; Yun-Fang Yang; Bryan J Simmons; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2015-03-20       Impact factor: 15.419

3.  Genomic and transcriptomic analyses of Agrobacterium tumefaciens S33 reveal the molecular mechanism of a novel hybrid nicotine-degrading pathway.

Authors:  Haiyan Huang; Wenjun Yu; Rongshui Wang; Huili Li; Huijun Xie; Shuning Wang
Journal:  Sci Rep       Date:  2017-07-06       Impact factor: 4.379

4.  Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

Authors:  Adam E Goetz; Neil K Garg
Journal:  Nat Chem       Date:  2012-11-25       Impact factor: 24.427

5.  General method for functionalized polyaryl synthesis via aryne intermediates.

Authors:  Thanh Truong; Milad Mesgar; Ky Khac Anh Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2014-06-03       Impact factor: 15.419

6.  6-hydroxy-3-succinoylpyridine hydroxylase catalyzes a central step of nicotine degradation in Agrobacterium tumefaciens S33.

Authors:  Huili Li; Kebo Xie; Haiyan Huang; Shuning Wang
Journal:  PLoS One       Date:  2014-07-23       Impact factor: 3.240

Review 7.  Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.

Authors:  Sarah M Anthony; Laura G Wonilowicz; Matthew S McVeigh; Neil K Garg
Journal:  JACS Au       Date:  2021-06-23
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.