Literature DB >> 19129907

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

Masafumi Ueda1, Maciej A A Walczak, Peter Wipf.   

Abstract

A tricyclic substructure of the tetracyclic nitrogen core of the daphniglaucins was formed by an oxidative activation of the allyl side chain of a bicyclo[1.1.0]butylmethylamine, a spontaneous intramolecular formal Alder-ene reaction, and a selective cyclization of a triol intermediate.

Entities:  

Year:  2008        PMID： 19129907      PMCID： PMC2575373          DOI： 10.1016/j.tetlet.2008.07.179

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


  18 in total

Review 1.  Recent development and application of chiral phase-transfer catalysts.

Authors:  Takuya Hashimoto; Keiji Maruoka
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

2.  Quaternary indole alkaloids from the stem bark of Strychnos guianensis.

Authors:  J Penelle; M Tits; P Christen; J Molgo; V Brandt; M Frédérich; L Angenot
Journal:  Phytochemistry       Date:  2000-04       Impact factor: 4.072

3.  Guiaflavine, a new bisindole quaternary alkaloid from the stem bark of Strychnos guianensis.

Authors:  J Penelle; M Tits; P Christen; V Brandt; M Frédérich; L Angenot
Journal:  J Nat Prod       Date:  1999-06       Impact factor: 4.050

4.  Daphniglaucins A and B, novel polycyclic quaternary alkaloids from Daphniphyllum glaucescens.

Authors:  Jun'ichi Kobayashi; Hiroshi Takatsu; Ya-Ching Shen; Hiroshi Morita
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

5.  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

6.  The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

Authors:  Martin J O'Donnell
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

7.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

8.  New antibacterial agents derived from the DNA gyrase inhibitor cyclothialidine.

Authors:  Peter Angehrn; Stefan Buchmann; Christoph Funk; Erwin Goetschi; Hans Gmuender; Paul Hebeisen; Dirk Kostrewa; Helmut Link; Thomas Luebbers; Raffaello Masciadri; Joergen Nielsen; Peter Reindl; Fabienne Ricklin; Anne Schmitt-Hoffmann; Frank-Peter Theil
Journal:  J Med Chem       Date:  2004-03-11       Impact factor: 7.446

9.  Two new quaternary alkaloids and anti-hepatitis B virus active constituents from Corydalis saxicola.

Authors:  Ying-Rui Wu; Yun-Bao Ma; You-Xing Zhao; Shu-Ying Yao; Jun Zhou; Ying Zhou; Ji-Jun Chen
Journal:  Planta Med       Date:  2007-07-05       Impact factor: 3.352

10.  Transition-metal-mediated cascade reactions: C,C-dicyclopropylmethylamines by way of double C,C-sigma-bond insertion into bicyclobutanes.

Authors:  Peter Wipf; Corey R J Stephenson; Kazuo Okumura
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419
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  3 in total

1.  Enantioselective synthesis of cyclobutanes via sequential Rh-catalyzed bicyclobutanation/Cu-catalyzed homoconjugate addition.

Authors:  Robert Panish; Srinivasa R Chintala; David T Boruta; Yinzhi Fang; Michael T Taylor; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419

2.  An ESR analysis of the mechanism of pericyclic reactions of bicyclobutane.

Authors:  Maciej A A Walczak; Byong-Kyu Shin; Peter Wipf; Sunil Saxena
Journal:  Org Biomol Chem       Date:  2009-04-06       Impact factor: 3.876

3.  Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity.

Authors:  Justin M Lopchuk; Kasper Fjelbye; Yu Kawamata; Lara R Malins; Chung-Mao Pan; Ryan Gianatassio; Jie Wang; Liher Prieto; James Bradow; Thomas A Brandt; Michael R Collins; Jeff Elleraas; Jason Ewanicki; William Farrell; Olugbeminiyi O Fadeyi; Gary M Gallego; James J Mousseau; Robert Oliver; Neal W Sach; Jason K Smith; Jillian E Spangler; Huichin Zhu; Jinjiang Zhu; Phil S Baran
Journal:  J Am Chem Soc       Date:  2017-02-20       Impact factor: 15.419
  3 in total

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