Literature DB >> 20845963

Total synthesis of the Aspidosperma alkaloid (±)-subincanadine F via a titanium-mediated intramolecular nucleophilic acyl substitution strategy.

Xiayun Cheng1, Chelsea M Duhaime, Stephen P Waters.   

Abstract

The total synthesis of the bridge-fused Aspidosperma indole alkaloid (±)-subincanadine F has been accomplished in seven steps. The synthetic utility of a titanium-mediated intramolecular nucleophilic acyl substitution (INAS) reaction for the construction of the bridge-fused ring system was demonstrated.

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Year:  2010        PMID： 20845963      PMCID： PMC2952173          DOI： 10.1021/jo1015823

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis.

Authors:  O G Kulinkovich; A de Meijere
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  Protecting-group-free total synthesis of (+/-)-subincanadine F.

Authors:  Pinhong Chen; Lidong Cao; Chaozhong Li
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

3.  Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2)-mediated ring opening and bridge-forming Mannich reaction.

Authors:  Peng Gao; Yanqin Liu; Lei Zhang; Peng-Fei Xu; Shaowu Wang; Yong Lu; Mingyuan He; Hongbin Zhai
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

4.  Subincanadines A-C, novel quaternary indole alkaloids from Aspidosperma subincanum.

Authors:  Jun'ichi Kobayashi; Mitsuhiro Sekiguchi; Sayaka Shimamoto; Hideyuki Shigemori; Haruaki Ishiyama; Ayumi Ohsaki
Journal:  J Org Chem       Date:  2002-09-06       Impact factor: 4.354
  4 in total

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