Literature DB >> 34176982

Rapid synthesis of the core scaffold of crinane and haemanthamine through a multi-component approach.

Nicholas P Massaro1, Joshua G Pierce1.   

Abstract

A rapid synthesis of the core structures of crinane and haemanthamine has been developed, enabled by a multicomponent approach. This work constitutes a formal synthesis of crinane and sets the stage for access to both families of natural products and key analogues. A key highlight of the approach is the modularity of the core synthesis, overcoming existing challenges for these scaffolds and providing a path to explore site-selective oxidation to expand the scope of molecules accessible from common intermediates.

Entities:  

Keywords:  Amaryllidaceae alkaloids; Heterocycles; Multicomponent; Natural Products; Total Synthesis

Year:  2021        PMID: 34176982      PMCID: PMC8224825          DOI: 10.1016/j.tetlet.2021.153201

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.032


  14 in total

1.  Total Synthesis of (±)-Crinane from 6,6-Dibromobicyclo[3.1.0]hexane Using a 5- exo- trig Radical Cyclization Reaction to Assemble the C3a-Arylated Perhydroindole Substructure.

Authors:  Ping Lan; Martin G Banwell; Anthony C Willis
Journal:  J Org Chem       Date:  2018-06-07       Impact factor: 4.354

Review 2.  Chemistry, biology, and medicinal potential of narciclasine and its congeners.

Authors:  Alexander Kornienko; Antonio Evidente
Journal:  Chem Rev       Date:  2008-05-20       Impact factor: 60.622

Review 3.  Amaryllidaceae and Sceletium alkaloids.

Authors:  Zhong Jin; Guangmin Yao
Journal:  Nat Prod Rep       Date:  2019-10-16       Impact factor: 13.423

4.  Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids.

Authors:  Nataliia V Shymanska; Joshua G Pierce
Journal:  Org Lett       Date:  2017-05-24       Impact factor: 6.005

5.  Stereoselective, Multicomponent Approach to Quaternary Substituted Hydroindole Scaffolds.

Authors:  Nicholas P Massaro; Joshua G Pierce
Journal:  Org Lett       Date:  2020-06-17       Impact factor: 6.005

6.  Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids.

Authors:  Ping Lan; Martin G Banwell; Anthony C Willis
Journal:  J Org Chem       Date:  2019-03-04       Impact factor: 4.354

7.  A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine.

Authors:  Masahiro Bohno; Hidetomo Imase; Noritaka Chida
Journal:  Chem Commun (Camb)       Date:  2004-03-30       Impact factor: 6.222

8.  Enantioselective synthesis of Amaryllidaceae alkaloids (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine.

Authors:  Meng-Xue Wei; Cheng-Tao Wang; Ji-Yuan Du; Hu Qu; Pei-Rong Yin; Xu Bao; Xiao-Yan Ma; Xian-He Zhao; Guo-Biao Zhang; Chun-An Fan
Journal:  Chem Asian J       Date:  2013-06-20

9.  Comparative Analysis of Amaryllidaceae Alkaloids from Three Lycoris Species.

Authors:  Yongqiang Tian; Chunyun Zhang; Mingquan Guo
Journal:  Molecules       Date:  2015-12-07       Impact factor: 4.411

Review 10.  Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids.

Authors:  Seydou Ka; Manoj Koirala; Natacha Mérindol; Isabel Desgagné-Penix
Journal:  Molecules       Date:  2020-10-23       Impact factor: 4.411

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