Issue 36, 2011
From the journal:

Chemical Communications

Total synthesis of (−)-nakadomarin A†

Andrew F. Kyle,a   Pavol Jakubec,a   Dane M. Cockfield,b   Ed Cleator,c   John Skidmored  and  Darren J. Dixon*a  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, United Kingdom
E-mail: darren.dixon@chem.ox.ac.uk
Tel: +44 1865 275648

b School of Chemistry, The University of Manchester, Manchester, United Kingdom

c Merck Sharp Dohme Research Laboratories, Global Process Research, Hoddesdon, Hertfordshire, United Kingdom

d GlaxoSmithKline, Neurosciences Centre of Excellence for Drug Discovery, New Frontiers Science Park, Harlow, United Kingdom

Abstract

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

Graphical abstract: Total synthesis of (−)-nakadomarin A

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Article information

DOI
https://doi.org/10.1039/C1CC13665H
Article type
Communication
Submitted
20 Jun 2011
Accepted
21 Jul 2011
First published
08 Aug 2011

Chem. Commun., 2011,47, 10037-10039

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Total synthesis of (−)-nakadomarin A

A. F. Kyle, P. Jakubec, D. M. Cockfield, E. Cleator, J. Skidmore and D. J. Dixon, Chem. Commun., 2011, 47, 10037 DOI: 10.1039/C1CC13665H

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