Artificial Molecular Rotors

Synthetic model compounds for hemoproteins

A highly convergent total synthesis of the spiroacetal macrolide (+)-milbemycinβ1

3. CheIatedHemes ......................................................................................................................... 127 3. A. Porphyrins HavingCovalently Attached Imidazole or Pyridine Ligands ......................................... 127 3.B. Porphyrins Having Covalently Attached Sulfur Ligands................................................................ 137 3.C. Porphyrins with Covalently Attached Ouinonc Groups ................................................................. 142 3. D. Porphvrins with Covalentlv Attached Interactive Groups .............................................................. 146

Synthesis and structure of biomimetic porphyrins

Bridged, capped and fenced porphyrins

Routes are developed for synthesis of porphyrins carrying functionalised bridges over the macrocycle; the FeII complexes of these products are of interest in relation to myoglobin and haemoglobin.

Synthetic sudies related to myoglobin: syntheses of bridged porphyrin systems

Synthetic routes to singly and doubly bridged porphyrins

The milbemycin β1 analogue (38) has been prepared by a convergent route involving the Wittig condensation between phosphonium salt (28) and 5-hydroxy-5H-furan-2-one (11), followed by diene isomerization, transprotection, lactonization, and reduction; the structure of the ester intermediate (37) was established by X-ray crystallography.

Synthesis of a macrocyclic analogue of milbemycin β1; X-ray structure of (1RS, 4RS, 6SR, 7SR, 19RS)-(10Z, 12E, 16E)-6,16-dimethyl-9-hydroxy-7-methoxy-10-methoxycarbonyl-2-oxatricyclo[17.3.1.04,9]tricosa-10,12,16-trien-3-one

Michael D. Turnbull

Papers

Synthetic sudies related to myoglobin: syntheses of bridged porphyrin systems

Synthetic routes to singly and doubly bridged porphyrins

Synthesis of a macrocyclic analogue of milbemycin β1; X-ray structure of (1RS, 4RS, 6SR, 7SR, 19RS)-(10Z, 12E, 16E)-6,16-dimethyl-9-hydroxy-7-methoxy-10-methoxycarbonyl-2-oxatricyclo[17.3.1.04,9]tricosa-10,12,16-trien-3-one