Literature DB >> 12605506

Total synthesis of (-)-aspidospermine via diastereoselective ring-closing olefin metathesis.

Yu-Ichi Fukuda1, Mitsuru Shindo, Kozo Shishido.   

Abstract

An enantiocontrolled total synthesis of (-)-aspidospermine has been achieved. The key element of the strategy is the diastereoselective construction of the quaternary stereogenic center employing 1,4-asymmetric induction during the ring-closing olefin metathesis.

Entities:  

Mesh：

Substances：

Year:  2003        PMID： 12605506     DOI： 10.1021/ol034020s

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


  9 in total

1.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

2.  Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.

Authors:  William H Pearson; Aaron Aponick
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

3.  Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.

Authors:  Rajesh Iyengar; Klaas Schildknegt; Martha Morton; Jeffrey Aubé
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

4.  Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine.

Authors:  James P Lajiness; Wanlong Jiang; Dale L Boger
Journal:  Org Lett       Date:  2012-04-05       Impact factor: 6.005

Review 5.  Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors:  Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

6.  Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst development inspired by natural product synthesis.

Authors:  Elizabeth S Sattely; Simon J Meek; Steven J Malcolmson; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

7.  Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

Authors:  Alyssa H Antropow; Nicholas R Garcia; Kolby L White; Mohammad Movassaghi
Journal:  Org Lett       Date:  2018-06-04       Impact factor: 6.005

Review 8.  Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation.

Authors:  Antoni Riera; María Moreno
Journal:  Molecules       Date:  2010-02-23       Impact factor: 4.411

9.  A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.

Authors:  Geoffrey M Giampa; Jian Fang; Matthias Brewer
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.