Literature DB >> 16355981

Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.

Rajesh Iyengar1, Klaas Schildknegt, Martha Morton, Jeffrey Aubé.   

Abstract

[reaction: see text] A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

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Year:  2005        PMID： 16355981      PMCID： PMC2525662          DOI： 10.1021/jo051212n

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


  13 in total

1.  Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine.

Authors:  R Iyengar; K Schildknegt; J Aubé
Journal:  Org Lett       Date:  2000-06-01       Impact factor: 6.005

2.  A combined intramolecular Diels-Alder/intramolecular schmidt reaction: formal synthesis of (+/-)-stenine.

Authors:  Jennifer E Golden; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2002-11-15       Impact factor: 15.336

Review 3.  Modern methods to produce natural-product libraries.

Authors:  Ulrich Abel; Corinna Koch; Michael Speitling; Friedrich G Hansske
Journal:  Curr Opin Chem Biol       Date:  2002-08       Impact factor: 8.822

4.  Total synthesis of (+/-)-aspidospermidine.

Authors:  M A Toczko; C H Heathcock
Journal:  J Org Chem       Date:  2000-05-05       Impact factor: 4.354

5.  Studies on the synthesis of Aspidosperma and related alkaloids. II. A synthetic approach to the C-21 oxygenated Aspidosperma alkaloids.

Authors:  I Inoue; Y Ban
Journal:  J Chem Soc Perkin 1       Date:  1970

6.  Total synthesis of aspidospermine.

Authors:  Y Ban; Y Sato; I Inoue; M Nagai; T Oishi; M Terashima; O Yonemitsu; Y Kanaoka
Journal:  Tetrahedron Lett       Date:  1965-07       Impact factor: 2.415

7.  Facile C-N cleavage in a series of bridged lactams.

Authors:  Yao Lei; Aaron D Wrobleski; Jennifer E Golden; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

8.  Exploiting the palladium[0]-catalysed Ullmann cross-coupling reaction in natural products chemistry: application to a total synthesis of the alkaloid (+/-)-aspidospermidine.

Authors:  Martin G Banwell; David W Lupton
Journal:  Org Biomol Chem       Date:  2004-12-07       Impact factor: 3.876

9.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

10.  Total synthesis of indole and dihydroindole alkaloids. V. The total synthesis of dl-quebrachamine and dl-aspidospermidine. A general entry into the aspidosperma alkaloids.

Authors:  J P Kutney; N Abdurahman; C Gletsos; P Le Quesne; E Piers; I Vlattas
Journal:  J Am Chem Soc       Date:  1970-03-25       Impact factor: 15.419
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  12 in total

1.  Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams.

Authors:  Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2007-02-16       Impact factor: 15.419

2.  Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.

Authors:  Hayato Ishikawa; Gregory I Elliott; Juraj Velcicky; Younggi Choi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

Review 3.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

4.  Enantioselective synthesis of the ABC ring motif of norzoanthamine based on asymmetric Robinson annulation reactions.

Authors:  Thong X Nguyen; Marianna Dakanali; Lynnie Trzoss; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2011-05-26       Impact factor: 6.005

5.  Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.

Authors:  William H Pearson; Aaron Aponick
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

6.  Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine.

Authors:  James P Lajiness; Wanlong Jiang; Dale L Boger
Journal:  Org Lett       Date:  2012-04-05       Impact factor: 6.005

7.  Synthesis, structural analysis, and reactivity of bridged orthoamides by intramolecular Schmidt reaction.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

8.  Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid.

Authors:  Yanmei Zhang; Greg Elliot; Adrian Saldanha; Igor Tsigelny; Dennis Carson; Wolf Wrasidlo
Journal:  Beilstein J Org Chem       Date:  2010-09-01       Impact factor: 2.883

9.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

10.  Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related Aspidosperma alkaloids.

Authors:  Marius Mewald; Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336
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