Literature DB >> 18855359

A concise asymmetric total synthesis of aspidophytine.

K C Nicolaou1, Stephen M Dalby, Utpal Majumder.   

Abstract

An expedient asymmetric total synthesis of aspidophytine is reported. A highly convergent strategy involving the sequential annulation of vinyl iodide 5 with indole 6 exploits varying modes of indole reactivity to provide aspidophytine in 23% over six steps from 5.

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Year:  2008        PMID： 18855359     DOI： 10.1021/ja806176w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 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

Review 3.  Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Authors:  Beau P Pritchett; Brian M Stoltz
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

4.  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

5.  Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Authors:  Beau P Pritchett; Etienne J Donckele; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-05       Impact factor: 15.336

6.  Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

Authors:  Zhi-Gang Xu; Shi-Qiang Li; Jiang-Ping Meng; Dian-Yong Tang; Liu-Jun He; Jie Lei; Hui-Kuan Lin; Hong-Yu Li; Zhong-Zhu Chen
Journal:  Chemistry       Date:  2018-04-20       Impact factor: 5.236

7.  Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (-)-Goniomitine, (+)-Aspidospermidine, and (-)-Quebrachamine.

Authors:  Beau P Pritchett; Jun Kikuchi; Yoshitaka Numajiri; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-26       Impact factor: 15.336

8.  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

9.  Iridium-catalyzed reductive nitro-Mannich cyclization.

Authors:  Alex W Gregory; Alan Chambers; Alison Hawkins; Pavol Jakubec; Darren J Dixon
Journal:  Chemistry       Date:  2014-11-14       Impact factor: 5.236

10.  Fates of imine intermediates in radical cyclizations of N-sulfonylindoles and ene-sulfonamides.

Authors:  Hanmo Zhang; E Ben Hay; Stephen J Geib; Dennis P Curran
Journal:  Beilstein J Org Chem       Date:  2015-09-17       Impact factor: 2.883
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