Literature DB >> 28496394

Triazaspirocycles: Occurrence, Synthesis, and Applications.

Claire M Gober1, Patrick J Carroll1, Madeleine M Joullié1.   

Abstract

Natural products bearing a triazaspirocyclic motif have received significant attention in recent years. These compounds, which feature three nitrogen atoms attached to one quaternary carbon forming a spirocyclic scaffold, exhibit a wide range of biological activity and have promising applications in materials as well as in drug discovery. In this review article, we will discuss triazaspirocycles in Nature, their biological activity, and applications. Methods for the synthesis of triazaspirocycles as well as the reactivity of triazaspirocyclic scaffolds will be reviewed.

Entities:  

Keywords:  1,3 Dipolar cycloaddition; N-heterocyclic carbene; cycloreversion; nitrogen heterocycles; spirocycles; triaza

Year:  2016        PMID: 28496394      PMCID: PMC5423685          DOI: 10.2174/1570193X13666160225001001

Source DB:  PubMed          Journal:  Mini Rev Org Chem        ISSN: 1570-193X            Impact factor:   2.495


  29 in total

1.  A concise stereoselective route to the indoline spiroaminal framework of neoxaline and oxaline.

Authors:  Toshiaki Sunazuka; Tatsuya Shirahata; Satoshi Tsuchiya; Tomoyasu Hirose; Ryuma Mori; Yoshihiro Harigaya; Isao Kuwajima; Satoshi Omura
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

2.  Asymmetric total synthesis of neoxaline.

Authors:  Tetsuya Ideguchi; Takeshi Yamada; Tatsuya Shirahata; Tomoyasu Hirose; Akihiro Sugawara; Yoshinori Kobayashi; Satoshi Ōmura; Toshiaki Sunazuka
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

3.  A single cluster of coregulated genes encodes the biosynthesis of the mycotoxins roquefortine C and meleagrin in Penicillium chrysogenum.

Authors:  Carlos García-Estrada; Ricardo V Ullán; Silvia M Albillos; María Ángeles Fernández-Bodega; Pawel Durek; Hans von Döhren; Juan F Martín
Journal:  Chem Biol       Date:  2011-11-23

4.  Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework.

Authors:  Takeshi Yamada; Tetsuya Ideguchi-Matsushita; Tomoyasu Hirose; Tatsuya Shirahata; Rei Hokari; Aki Ishiyama; Masato Iwatsuki; Akihiro Sugawara; Yoshinori Kobayashi; Kazuhiko Otoguro; Satoshi Ōmura; Toshiaki Sunazuka
Journal:  Chemistry       Date:  2015-07-06       Impact factor: 5.236

5.  Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities.

Authors:  Lin Du; Teng Feng; Boyu Zhao; Dehai Li; Shengxin Cai; Tianjiao Zhu; Fengping Wang; Xiang Xiao; Qianqun Gu
Journal:  J Antibiot (Tokyo)       Date:  2010-02-26       Impact factor: 2.649

6.  Alkyne and reversible nitrile activation: N,N'-diamidocarbene-facilitated synthesis of cyclopropenes, cyclopropenones, and azirines.

Authors:  Jonathan P Moerdyk; Christopher W Bielawski
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

7.  [4 + 1] cycloaddition of N-heterocyclic carbenes with vinyl isocyanates.

Authors:  James H Rigby; Zhengqiang Wang
Journal:  Org Lett       Date:  2002-11-28       Impact factor: 6.005

8.  Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway.

Authors:  Marco I Ries; Hazrat Ali; Peter P Lankhorst; Thomas Hankemeier; Roel A L Bovenberg; Arnold J M Driessen; Rob J Vreeken
Journal:  J Biol Chem       Date:  2013-11-13       Impact factor: 5.157

9.  Extending Pummerer reaction chemistry: (+/-)-dibromoagelaspongin synthesis and related studies.

Authors:  Ken S Feldman; Matthew D Fodor
Journal:  J Org Chem       Date:  2009-05-01       Impact factor: 4.354

10.  A branched biosynthetic pathway is involved in production of roquefortine and related compounds in Penicillium chrysogenum.

Authors:  Hazrat Ali; Marco I Ries; Jeroen G Nijland; Peter P Lankhorst; Thomas Hankemeier; Roel A L Bovenberg; Rob J Vreeken; Arnold J M Driessen
Journal:  PLoS One       Date:  2013-06-12       Impact factor: 3.240

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  1 in total

1.  Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosynthetic pathway.

Authors:  Sean A Newmister; Stelamar Romminger; Jennifer J Schmidt; Robert M Williams; Janet L Smith; Roberto G S Berlinck; David H Sherman
Journal:  Org Biomol Chem       Date:  2018-09-11       Impact factor: 3.876

  1 in total

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