Literature DB >> 33828342

A concise Diels-Alder strategy leading to congeners of the ABC ring system of the marine alkaloid 'upenamide.

Marta E Wenzler1, Bruce J Melancon1, Gary A Sulikowski1.   

Abstract

A second-generation approach to the BC spirocycle of 'upenamide is reported. Central to the synthesis is an endo selective Diels-Alder reaction between 1-(t-butyldimethylsiloxy)-1,3-butadiene and bromomaleic anhydride followed by a radical mediated allylation of the ring fusion bromide. Functional group manipulation provides three (9-11) advanced synthetic intermediates ready for coupling with the remaining half (DE bicycle) of 'upenamide.

Entities:  

Keywords:  Diels–Alder; Hemiaminal; Quaternary stereocenter; Staudinger reaction; Stereocontrol

Year:  2016        PMID： 33828342      PMCID： PMC8023302          DOI： 10.1016/j.tetlet.2016.05.102

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  7 in total

1.  'Upenamide: An unprecedented macrocyclic alkaloid from the Indonesian sponge Echinochalina sp.

Authors:  J I Jiménez; G Goetz; C M Mau; W Y Yoshida; P J Scheuer; R T Williamson; M Kelly
Journal:  J Org Chem       Date:  2000-12-15       Impact factor: 4.354

2.  Stereocontrolled synthesis of the DE ring system of the marine alkaloid upenamide.

Authors:  Kurt Kiewel; Zhushou Luo; Gary A Sulikowski
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

3.  Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.

Authors:  Zhushou Luo; Katherine Peplowski; Gary A Sulikowski
Journal:  Org Lett       Date:  2007-11-01       Impact factor: 6.005

Review 4.  'Upenamide: trials and tribulations.

Authors:  William P Unsworth; Richard J K Taylor
Journal:  Org Biomol Chem       Date:  2013-11-14       Impact factor: 3.876

5.  Direct imine acylation: synthesis of the proposed structures of 'upenamide.

Authors:  William P Unsworth; Katherine A Gallagher; Mickaël Jean; Jan Peter Schmidt; Louis J Diorazio; Richard J K Taylor
Journal:  Org Lett       Date:  2012-12-24       Impact factor: 6.005

6.  Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.

Authors:  P A Wender; F C Bi; M A Brodney; F Gosselin
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

7.  The first synthesis of the ABC-ring system of 'upenamide.

Authors:  Jan Peter Schmidt; Sandra Beltrán-Rodil; Rhona J Cox; Graeme D McAllister; Mark Reid; Richard J K Taylor
Journal:  Org Lett       Date:  2007-09-01       Impact factor: 6.005
  7 in total

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