Literature DB >> 19105659

Enantioselective sequential conjugate addition-allylation reactions: a concise total synthesis of (+)-podophyllotoxin.

Yingming Wu1, Jingfeng Zhao, Jingbo Chen, Chengxue Pan, Liang Li, Hongbin Zhang.   

Abstract

A highly flexible and concise total synthesis of (+)-podophyllotoxin featured with an enantioselective sequential conjugate addition-allylation reaction was reported. Starting from commercially available 3,4,5-trimethoxycinnamic acid, this new route leads to (+)-podophyllotoxin 1 in only eight steps with 29% overall yield.

Entities:  

Mesh:

Substances:

Year:  2009        PMID: 19105659     DOI: 10.1021/ol8026208

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


  6 in total

1.  Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Wendy Wen Yi Leong; Benjamin R Taft; Daniel V Krogstad
Journal:  J Org Chem       Date:  2011-05-19       Impact factor: 4.354

2.  Asymmetric Chemoenzymatic Synthesis of (-)-Podophyllotoxin and Related Aryltetralin Lignans.

Authors:  Jian Li; Xiao Zhang; Hans Renata
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-17       Impact factor: 15.336

Review 3.  Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

Authors:  Rebekah G Reynolds; Huong Quynh Anh Nguyen; Jordan C T Reddel; Regan J Thomson
Journal:  Nat Prod Rep       Date:  2022-03-23       Impact factor: 13.423

4.  Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins.

Authors:  Bing-Feng Sun; Ran Hong; Yan-Biao Kang; Li Deng
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

5.  Investigation and Expression of the Secoisolariciresinol Dehydrogenase Gene Involved in Podophyllotoxin Biosynthesis.

Authors:  Sonja L B Arneaud; John R Porter
Journal:  Mol Biotechnol       Date:  2015-12       Impact factor: 2.695

Review 6.  Advancing the Logic of Chemical Synthesis: C-H Activation as Strategic and Tactical Disconnections for C-C Bond Construction.

Authors:  Nelson Y S Lam; Kevin Wu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-04       Impact factor: 16.823

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.