Issue 12, 2004
From the journal:

Organic & Biomolecular Chemistry

The nucleophilic addition of α-metallated 1,3-dioxanes to planar chiral cationic η3-allylmolybdenum complexes. Synthesis of (2E,5S,6R,7E)-6-methyl-8-phenylocta-2,7-dienoic acid methyl ester, a key component of the Cryptophycins

John Cooksey,a   Andrew Gunn,a   Philip J. Kocienski,*a   Alexander Kuhl,b   Sukhjinder Uppal,a   John A. Christopherbc  and  Richard Bellc  

* Corresponding authors

a Department of Chemistry, Leeds University, Leeds, UK

b Department of Chemistry, Glasgow University, Glasgow, UK

c GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, UK

Abstract

Two adjacent stereogenic centres and a pendant alkene were constructed via nucleophilic addition of a 1,3-dioxan-4-ylcopper(I) reagent to a cationic η3-allylmolybdenum complex as part of a synthesis of (2E,5S,6R,7E)-6-methyl-8-phenylocta-2,7-dienoic acid, a key component of the Cryptophycins. Oxidative addition of Mo(CO)4(THF)2 to allyl benzoates provides an efficient synthesis of η3-allylmolybdenum(dicarbonyl) complexes.

Graphical abstract: The nucleophilic addition of α-metallated 1,3-dioxanes to planar chiral cationic η3-allylmolybdenum complexes. Synthesis of (2E,5S,6R,7E)-6-methyl-8-phenylocta-2,7-dienoic acid methyl ester, a key component of the Cryptophycins

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Article information

DOI
https://doi.org/10.1039/B400242C
Article type
Paper
Submitted
09 Jan 2004
Accepted
06 Apr 2004
First published
25 May 2004

Org. Biomol. Chem., 2004,2, 1719-1731

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The nucleophilic addition of α-metallated 1,3-dioxanes to planar chiral cationic η3-allylmolybdenum complexes. Synthesis of (2E,5S,6R,7E)-6-methyl-8-phenylocta-2,7-dienoic acid methyl ester, a key component of the Cryptophycins

J. Cooksey, A. Gunn, P. J. Kocienski, A. Kuhl, S. Uppal, J. A. Christopher and R. Bell, Org. Biomol. Chem., 2004, 2, 1719 DOI: 10.1039/B400242C

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