Literature DB >> 16836384

Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

José M Mejía-Oneto1, Albert Padwa.   

Abstract

[Structure: see text] A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.

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Year:  2006        PMID： 16836384      PMCID： PMC2604816          DOI： 10.1021/ol061137i

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 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.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

3.  Intramolecular [3 + 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems.

Authors:  José M Mejía-Oneto; Albert Padwa
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

4.  Synthetic Applications of 2-(1,3-Dithian-2-yl)indoles. 7. Synthesis of Aspidospermidine.

Authors:  Pilar Forns; Anna Diez; Mario Rubiralta
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

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

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

6.  Cycloaddition chemistry of 2-vinyl-substituted indoles and related heteroaromatic systems.

Authors:  Albert Padwa; Stephen M Lynch; José M Mejía-Oneto; Hongjun Zhang
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

7.  Synthesis of the Pentacyclic Skeleton of the Aspidosperma Alkaloids Using Rhodium Carbenoids as Reactive Intermediates.

Authors:  Albert Padwa; Alan T. Price
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

8.  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

9.  Enantioselective total synthesis of aspidophytine.

Authors:  Shinjiro Sumi; Koji Matsumoto; Hidetoshi Tokuyama; Tohru Fukuyama
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

10.  A new strategy toward indole alkaloids involving an intramolecular cycloaddition/rearrangement cascade.

Authors:  Albert Padwa; Michael A Brodney; Stephen M Lynch; Paitoon Rashatasakhon; Qiu Wang; Hongjun Zhang
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354
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  12 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine.

Authors:  Arun K Ghosh; Joshua R Born; Luke A Kassekert
Journal:  J Org Chem       Date:  2019-04-02       Impact factor: 4.354

3.  The Domino Way to Heterocycles.

Authors:  Albert Padwa; Scott K Bur
Journal:  Tetrahedron       Date:  2007-06-18       Impact factor: 2.457

4.  Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids.

Authors:  Xuechuan Hong; Stefan France; José M Mejía-Oneto; Albert Padwa
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

5.  Total synthesis of (+)-fendleridine (aspidoalbidine) and (+)-1-acetylaspidoalbidine.

Authors:  Erica L Campbell; Andrea M Zuhl; Christopher M Liu; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

6.  Lewis acid-promoted alpha-hydroxy beta-dicarbonyl to alpha-ketol ester rearrangement.

Authors:  Xuechuan Hong; José M Mejía-Oneto; Albert Padwa
Journal:  Tetrahedron Lett       Date:  2006-11-20       Impact factor: 2.415

7.  A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.

Authors:  Xuechuan Hong; Stefan France; Albert Padwa
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

8.  The Rhodium(II) Carbenoid Cyclization-Cycloaddition Cascade of alpha-Diazo Dihydroindolinones for the Synthesis of Novel Azapolycyclic Ring Systems.

Authors:  Dylan B England; James M Eagan; Gokce Merey; Olcay Anac; Albert Padwa
Journal:  Tetrahedron       Date:  2008-02-04       Impact factor: 2.457

9.  Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade.

Authors:  Dylan B England; Albert Padwa
Journal:  Org Lett       Date:  2007-07-21       Impact factor: 6.005

10.  Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine via Late-Stage Oxidation of (+)-Fendleridine Derivatives.

Authors:  Kolby L White; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-08-26       Impact factor: 15.419
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