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Title
| - Efficient Generation of a Trisporoid Library by Combination ofSynthesis and Biotransformation
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Abstract
| - Trisporic acids and their biosynthetic precursors represent a family of powerful fungal pheromones andmorphogenetic factors. A highly flexible synthetic protocol is described that (i) provides rapid access tononfunctionalized early trisporoids from β-ionone, (ii) includes a regiospecific oxidative functionalizationof β-ionone leading to 1-acetoxy-β-ionone giving access to functionalized trisporoids, and (iii) utilizesa biotransformation of early synthetic trisporoids by growing cells of Blakeslea trispora to prepare latetrisporoids including trisporic acids. The same protocol also provides deuterium-labeled trisporoids suchas trisporin B [2H3]-19. Administration of [2H3]-19 to growing cells of the (−)-mating type of B. trisporaresulted in the formation of the labeled trisporols [2H3]-20 and [2H3]-21. Growing cultures containingboth mating types can be used to prepare trisporic acids from early precursors.
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