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Synthesis of novel antifungal agents - concise construction of lanomycin and related compounds


There is need for the control of fungal pathogens in human medicine and agriculture. Lanomycin, isolated from Pycnidiophora dispersa, is a promising lead for the development of novel antifungal agents. The compound was shown to inhibit the P450 enzyme lanosterol 14a-de- methylase. It selectively inhibits some Candida species.
In this project a simple, general and stereoselective method for the elaboration of lanomycin and related molecules shall be established. The synthesis contains two crucial novel transformations: A dienyl borane shall be used to enantioselectively build two of the stereocenters of the target compound. An allene will be the product of this reaction. This compound might then be cyclised oxidatively to yield a B-ethynyl-pyranoside. There are good indirect reasons to expect that both steps can be realised but, if needed, there are many fall back options. The side chain of the molecule will then be completed by a methylzirconation-palladium catalysed coupling sequence.
It is planned to synthesize diverse analogues of lanomycin for bio-assa Therefore, it will be helpful to adapt this chemistry for polymer supported combinatorial synthesis. The activity results will then point at compounds of increased stability and potency.


South Kensington
SW7 2AZ London
United Kingdom

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