Literature DB >> 24595901

Strategies towards the synthesis of calyciphylline A-type Daphniphyllum alkaloids.

Baldip Kang1, Pavol Jakubec, Darren J Dixon.   

Abstract

The Daphniphyllum alkaloids are a diverse family of natural products rich in number and structural diversity that have been known for many decades. However, the structurally unique subclass of calyciphylline A-type alkaloids has only recently been discovered and is relatively unexplored. Several noteworthy core syntheses and the development of a wide range of novel synthetic strategies have been achieved. This includes strategies based on intramolecular Michael addition, Pd-catalysis, cycloaddition, and Mannich-type reactions. This review will provide an overview of these synthetic studies.

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Year:  2014        PMID： 24595901     DOI： 10.1039/c3np70115h

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN： 0265-0568            Impact factor:   13.423


  9 in total

1.  Calyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H and (-)-Isodaphlongamine H.

Authors:  Cedric L Hugelshofer; Vignesh Palani; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-05-16       Impact factor: 15.419

2.  Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations.

Authors:  Jennifer L Stockdill; Alberto M Lopez; Ahmad A Ibrahim
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Tin-Free Access to the ABC Core of the Calyciphylline A Alkaloids and Unexpected Formation of a D-Ring-Contracted Tetracyclic Core.

Authors:  Alberto M Lopez; Ahmad A Ibrahim; Gregory J Rosenhauer; Hansamali S Sirinimal; Jennifer L Stockdill
Journal:  Org Lett       Date:  2018-04-03       Impact factor: 6.005

Review 4.  Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Authors:  Martin Büschleb; Stéphane Dorich; Stephen Hanessian; Daniel Tao; Kyle B Schenthal; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

5.  The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.

Authors:  Artem Shvartsbart; Amos B Smith
Journal:  J Am Chem Soc       Date:  2015-03-10       Impact factor: 15.419

6.  Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.

Authors:  Adam D Gammack Yamagata; Swarup Datta; Kelvin E Jackson; Linus Stegbauer; Robert S Paton; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

7.  Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J.

Authors:  Yan Zhang; Jingping Hu; Lian-Dong Guo; Chengqing Ning; Heyifei Fu; Yuye Chen; Jing Xu
Journal:  Nat Commun       Date:  2020-07-15       Impact factor: 14.919

8.  Site-Selective Reaction of Enaminones and Enamine Esters for the Synthesis of Novel Diverse Morphan Derivatives.

Authors:  Xing-Mei Hu; Bei Zhou; Chang-Long Yang; Jun Lin; Sheng-Jiao Yan
Journal:  ACS Omega       Date:  2018-06-04

9.  Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework.

Authors:  Keita Komine; Kyle M Lambert; Quentin R Savage; Joshua B Cox; John L Wood
Journal:  Chem Sci       Date:  2020-07-30       Impact factor: 9.825
  9 in total

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