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

Organic & Biomolecular Chemistry Pub Date: 2004-05-25 DOI: 10.1039/B400242C

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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