Literature DB >> 12201766

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

Jun'ichi Kobayashi1, Mitsuhiro Sekiguchi, Sayaka Shimamoto, Hideyuki Shigemori, Haruaki Ishiyama, Ayumi Ohsaki.   

Abstract

Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means.

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Year:  2002        PMID: 12201766     DOI: 10.1021/jo025854b

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


  5 in total

1.  Relaxant effect and possible mechanism of 17-nor-subincanadine E in rabbit corpora cavernosa.

Authors:  Otacilio D Benvindo; Nilberto Rf Nascimento; Claudia F Santos; Manasses C Fonteles; Edilberto R Silveira; Daniel E Uchoa; Adriana R Campos; Karina Ma Cunha; Flavia A Santos; Vietla S Rao
Journal:  Asian J Androl       Date:  2011-07-18       Impact factor: 3.285

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

Authors:  Xiayun Cheng; Chelsea M Duhaime; Stephen P Waters
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

3.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

4.  Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins.

Authors:  Masafumi Ueda; Maciej A A Walczak; Peter Wipf
Journal:  Tetrahedron Lett       Date:  2008-06       Impact factor: 2.415

Review 5.  Samarium(ii) iodide-mediated reactions applied to natural product total synthesis.

Authors:  Majid M Heravi; Azadeh Nazari
Journal:  RSC Adv       Date:  2022-03-30       Impact factor: 3.361

  5 in total

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