Indoles prenyl

Keywords Alkaloids Indole Prenylation Regioselectivity Total synthesis Contents... 

Li and co-workers expressed the prenyltransferase His6-FtmPT2 from Aspergillus fumigatus (2 mg/L culture) [36], which uses ammonium prenylpyrophosphate (8) as prenyl source. After 2 h at 37 °C, about one third of 9 had been converted to 10. Since then, the Li group has contributed many more and higher yielding examples of enzymatic indole prenylation (see below). 

Chemoenzymatic synthesis. Enzymatic prenylation of indole will probably soon become practical in a chemical sense with general availability of indole prenyl-transferases. N-ferf-Prenylation of L-tryptophan (18) was possible employing the cyclic dipeptide prenyltransferase CdpNPT from Aspergillus fumigatus affording N-ferf-prenyltryptophan 19 (38%, Scheme 5) [41]. A prenyl transferase from Aspergillus oryzae catalysed the simultaneous N-ferf-prenylation and 7-prenylation of the diketopiperazine cyclo-L-Trp-L-Trp [43]. 

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