Literature DB >> 30614709

A Complementary Process to Pauson-Khand-Type Annulation Reactions for the Construction of Fully Substituted Cyclopentenones.

Adam B Millham1, Matthew J Kier1, Robert M Leon1, Rajdip Karmakar1, Zachary D Stempel1, Glenn C Micalizio1.   

Abstract

A complementary process to the Pauson-Khand annulation is described that is well suited to forging densely substituted/oxygenated cyclopentenone products (including fully substituted variants). The reaction is thought to proceed through a sequence of metallacycle-mediated bond-forming events that engages an internal alkyne and a β-keto ester in an annulation process that forges two C-C bonds. A variant of this annulation process has also been established that delivers deoxygenated cyclopentenones that lack the allylic tertiary alcohol.

Entities:  

Mesh:

Substances:

Year:  2019        PMID: 30614709      PMCID: PMC6465167          DOI: 10.1021/acs.orglett.8b03922

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


  20 in total

Review 1.  Trends in applying C-H oxidation to the total synthesis of natural products.

Authors:  Yuanyou Qiu; Shuanhu Gao
Journal:  Nat Prod Rep       Date:  2016-02-05       Impact factor: 13.423

2.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  C-H functionalization logic in total synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  Chem Soc Rev       Date:  2011-02-07       Impact factor: 54.564

4.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

Review 5.  Toward the ideal synthesis and molecular function through synthesis-informed design.

Authors:  Paul A Wender
Journal:  Nat Prod Rep       Date:  2014-03-03       Impact factor: 13.423

6.  Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation.

Authors:  W J Kerr; M McLaughlin; A J Morrison; P L Pauson
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

7.  14-step synthesis of (+)-ingenol from (+)-3-carene.

Authors:  Lars Jørgensen; Steven J McKerrall; Christian A Kuttruff; Felix Ungeheuer; Jakob Felding; Phil S Baran
Journal:  Science       Date:  2013-08-01       Impact factor: 47.728

8.  Intramolecular Pauson-Khand reactions of methylenecyclopropane and bicyclopropylidene derivatives as an approach to spiro(cyclopropanebicyclo[n.3.0]alkenones).

Authors:  Armin de Meijere; Heike Becker; Andreas Stolle; Sergei I Kozhushkov; M Teresa Bes; Jacques Salaün; Mathias Noltemeyer
Journal:  Chemistry       Date:  2005-04-08       Impact factor: 5.236

9.  Metallacycle-Mediated Cross-Coupling with Substituted and Electronically Unactivated Alkenes.

Authors:  Holly A Reichard; Glenn C Micalizio
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

10.  Total synthesis of eudesmane terpenes by site-selective C-H oxidations.

Authors:  Ke Chen; Phil S Baran
Journal:  Nature       Date:  2009-05-13       Impact factor: 49.962

View more
  3 in total

1.  Synthesis of Anhydroryanodol.

Authors:  Kang Du; Matthew J Kier; Zachary D Stempel; Valer Jeso; Arnold L Rheingold; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2020-07-07       Impact factor: 15.419

2.  Studies Targeting Ryanodol Result in an Annulation Reaction for the Synthesis of a Variety of Fused Carbocycles.

Authors:  Rajdip Karmakar; Arnold L Rheingold; Glenn C Micalizio
Journal:  Org Lett       Date:  2019-07-12       Impact factor: 6.005

3.  Oxygenated Cyclopentenones via the Pauson-Khand Reaction of Silyl Enol Ether Substrates.

Authors:  Paul Shaw; Storm J Hassell-Hart; Gayle E Douglas; Andrew G Malcolm; Alan R Kennedy; Gemma V White; Laura C Paterson; William J Kerr
Journal:  Org Lett       Date:  2022-04-04       Impact factor: 6.072

  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.