Literature DB >> 21826301

Total synthesis of (-)-nakadomarin A.

Andrew F Kyle1, Pavol Jakubec, Dane M Cockfield, Ed Cleator, John Skidmore, Darren J Dixon.   

Abstract

A highly diastereoselective bifunctional organocatalyst controlled Michael addition, a nitro-Mannich/lactamization cascade, a furan N-acyliminium cyclisation, a sequential alkyne RCM/syn-reduction and an alkene RCM has allowed a 19 step, highly stereoselective synthesis of (-)-nakadomarin A.

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Year:  2011        PMID： 21826301     DOI： 10.1039/c1cc13665h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 in total

1.  Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A.

Authors:  Chenbo Wang; Miao Yu; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Chemistry       Date:  2013-01-23       Impact factor: 5.236

2.  Lithium Enolates Derived from Pyroglutaminol: Aggregation, Solvation, and Atropisomerism.

Authors:  Michael J Houghton; Naomi A Biok; Christopher J Huck; Russell F Algera; Ivan Keresztes; Stephen W Wright; David B Collum
Journal:  J Org Chem       Date:  2016-04-25       Impact factor: 4.354

3.  A Unified Approach to Polycyclic Alkaloids of the Ingenamine Estate: Total Syntheses of Keramaphidin B, Ingenamine, and Nominal Njaoamine I.

Authors:  Zhanchao Meng; Simon M Spohr; Sandra Tobegen; Christophe Farès; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-08-27       Impact factor: 15.419

4.  Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step.

Authors:  James C Anderson; Andreas S Kalogirou; Michael J Porter; Graham J Tizzard
Journal:  Beilstein J Org Chem       Date:  2013-08-23       Impact factor: 2.883

5.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354

6.  Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy.

Authors:  Jai K Chavda; Panayiotis A Procopiou; Peter N Horton; Simon J Coles; Michael J Porter
Journal:  European J Org Chem       Date:  2013-11-14

7.  Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine.

Authors:  Zhanchao Meng; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419
  7 in total

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