1024014-00-3Relevant academic research and scientific papers
The cascade radical cyclisation approach to prenylated alkaloids: Synthesis of stephacidin A and notoamide B
Simpkins, Nigel S.,Pavlakos, Ilias,Weller, Michael D.,Male, Louise
, p. 4957 - 4970 (2013/08/23)
A strategy for the synthesis of members of the prenylated indole alkaloid family is described, which involves a radical cascade process of an appropriately substituted diketopiperazine (DKP) core structure. Several approaches to the generation of the initial radical were explored, with the most successful involving treatment of a sulfenyl substituted DKP under classical reductive conditions by heating with Bu3SnH and a radical initiator. The required, fully substituted, radical precursor DKP structures were prepared using regio- and stereocontrolled enolate chemistry of simpler proline-tryptophan derived DKPs. The new approach allowed rapid access to a key polycyclic indoline structure, which was converted into either of the natural products stephacidin A or notoamide B.
