Literature DB >> 19397370

Total synthesis of (-)-acutumine.

Fang Li1, Samuel S Tartakoff, Steven L Castle.   

Abstract

The first total synthesis of the tetracyclic alkaloid (-)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and the Lewis acid-promoted cyclization of an amine onto an alpha,beta-unsaturated dimethyl ketal.

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Year:  2009        PMID： 19397370     DOI： 10.1021/ja9024403

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


  12 in total

1.  Enantioselective conjugate allylation of cyclic enones.

Authors:  Douglass F Taber; David A Gerstenhaber; James F Berry
Journal:  J Org Chem       Date:  2011-08-23       Impact factor: 4.354

2.  Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.

Authors:  Zhiwei Yin; Jinzhu Zhang; Jing Wu; Riana Green; Sihan Li; Shengping Zheng
Journal:  Org Biomol Chem       Date:  2014-05-14       Impact factor: 3.876

3.  Rapid construction of the aza-propellane core of acutumine via a photochemical [2 + 2] cycloaddition reaction.

Authors:  Raul Navarro; Sarah E Reisman
Journal:  Org Lett       Date:  2012-08-14       Impact factor: 6.005

Review 4.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

5.  Enantioselective total synthesis of (-)-acutumine.

Authors:  Fang Li; Samuel S Tartakoff; Steven L Castle
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

6.  The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols.

Authors:  David S Barnett; Philip N Moquist; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 7.  Total synthesis of complex terpenoids employing radical cascade processes.

Authors:  Kevin Hung; Xirui Hu; Thomas J Maimone
Journal:  Nat Prod Rep       Date:  2018-02-21       Impact factor: 13.423

Review 8.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

Review 9.  Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Authors:  Martin Büschleb; Stéphane Dorich; Stephen Hanessian; Daniel Tao; Kyle B Schenthal; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

10.  Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization-Carbonylation-Alkynylation.

Authors:  Youai Qiu; Bin Yang; Can Zhu; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419
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