Literature DB >> 26028789

Atropurpuran - Missing Biosynthetic Link Leading to the Hetidine and Arcutine C20-Diterpenoid Alkaloids or an Oxidative Degradation Product?

Manuel Weber1, Kyle Owens1, Richmond Sarpong1.   

Abstract

A possible biosynthetic link between atropurpuran, the hetidine diterpenoid alkaloids and the alkaloid arcutine and congeners is proposed. The feasibility of aspects of this biosynthesis, especially key 1,2-rearrangements, have been examined computationally.

Entities:  

Keywords:  Biosynthesis; arcutines; diterpenoid alkaloids; hetidine; oxidation

Year:  2015        PMID: 26028789      PMCID: PMC4445844          DOI: 10.1016/j.tetlet.2015.01.111

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  10 in total

Review 1.  C20-diterpenoid alkaloids.

Authors:  Feng-Peng Wang; Xiao-Tian Liang
Journal:  Alkaloids Chem Biol       Date:  2002

2.  The C19-diterpenoid alkaloids.

Authors:  Feng-Peng Wang; Qiao-Hong Chen
Journal:  Alkaloids Chem Biol       Date:  2010

Review 3.  Structural biology and chemistry of the terpenoid cyclases.

Authors:  David W Christianson
Journal:  Chem Rev       Date:  2006-08       Impact factor: 60.622

4.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

Review 5.  Biosynthesis via carbocations: theoretical studies on terpene formation.

Authors:  Dean J Tantillo
Journal:  Nat Prod Rep       Date:  2011-05-04       Impact factor: 13.423

6.  Formation of beyerene, kaurene, trachylobane, and atiserene diterpenes by rearrangements that avoid secondary carbocations.

Authors:  Young J Hong; Dean J Tantillo
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

7.  Switching between concerted and stepwise mechanisms for dyotropic rearrangements of β-lactones leading to spirocyclic, bridged γ-butyrolactones.

Authors:  Rebecca L Davis; Carolyn A Leverett; Daniel Romo; Dean J Tantillo
Journal:  J Org Chem       Date:  2011-08-04       Impact factor: 4.354

Review 8.  Modern synthetic efforts toward biologically active terpenes.

Authors:  Thomas J Maimone; Phil S Baran
Journal:  Nat Chem Biol       Date:  2007-07       Impact factor: 15.040

9.  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

10.  Approach to the biosynthesis of atisine-type diterpenoid alkaloids.

Authors:  Pei-Ji Zhao; Suo Gao; Li-Ming Fan; Jing-Lei Nie; Hong-Ping He; Ying Zeng; Yue-Mao Shen; Xiao-Jiang Hao
Journal:  J Nat Prod       Date:  2009-04       Impact factor: 4.050

  10 in total
  6 in total

1.  Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis.

Authors:  Kyle R Owens; Shelby V McCowen; Katherine A Blackford; Sohei Ueno; Yasuo Hirooka; Manuel Weber; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

Review 2.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

Review 3.  Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.

Authors:  Bastien Delayre; Qian Wang; Jieping Zhu
Journal:  ACS Cent Sci       Date:  2021-04-08       Impact factor: 14.553

Review 4.  Non-alkaloidal constituents from the genus Aconitum: a review.

Authors:  Tianpeng Yin; Hao Zhou; Le Cai; Zhongtao Ding
Journal:  RSC Adv       Date:  2019-04-02       Impact factor: 4.036

Review 5.  Retrosynthetic strategies and their impact on synthesis of arcutane natural products.

Authors:  Shelby V McCowen; Nicolle A Doering; Richmond Sarpong
Journal:  Chem Sci       Date:  2020-04-21       Impact factor: 9.825

6.  Total synthesis of atropurpuran.

Authors:  Jing Gong; Huan Chen; Xiao-Yu Liu; Zhi-Xiu Wang; Wei Nie; Yong Qin
Journal:  Nat Commun       Date:  2016-07-08       Impact factor: 14.919

  6 in total

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