Literature DB >> 23859604

Construction of the tricyclic A-B-C core of the Veratrum alkaloids.

Douglass F Taber1, James F Berry.   

Abstract

Organocatalyzed enantioselective allylation of 2-iodocyclohexenone followed by methylation and oxy-Cope rearrangement delivered enantiomerically enriched 2-methyl 3-allyl cyclohexanone, which engaged in acid-catalyzed Robinson annulation to give the bicyclic enone. Subsequent elaboration of the pendant allyl group into an α-diazo β-keto ester set the stage for Rh-mediated cyclization to deliver the tricyclic A-B-C core of the Veratrum alkaloids.

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Year:  2013        PMID： 23859604      PMCID： PMC4255024          DOI： 10.1021/jo401158d

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


  13 in total

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3.  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

4.  Suzuki cross-coupling/reductive debenzyloxycarbonylation sequence for the syntheses of [c]annulated isoquinolines: application for the syntheses of pancratistatin-like isoquinolines.

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Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

5.  Synthesis of Bis-18,18'-desmethyl Ritterazine N.

Authors:  Douglass F Taber; Jean-Michel Joerger
Journal:  J Org Chem       Date:  2008-05-08       Impact factor: 4.354

6.  The synthesis and preliminary biological evaluation of a novel steroid with neurotrophic activity: NGA0187.

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7.  Silver-catalyzed asymmetric Sakurai-Hosomi allylation of ketones.

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Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

8.  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

9.  Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.

Authors:  Douglass F Taber; Karen V Taluskie
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

10.  A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant: application to classically challenging substrates.

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Journal:  J Am Chem Soc       Date:  2009-05-06       Impact factor: 15.419
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  4 in total

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Authors:  Daniel W Robbins; KyungA Lee; Daniel L Silverio; Alexey Volkov; Sebastian Torker; Amir H Hoveyda
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Journal:  J Am Chem Soc       Date:  2019-02-01       Impact factor: 15.419

4.  Enantioselective Total Synthesis of (+)-Heilonine.

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  4 in total

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